JPH0892275A - Modified oligodeoxyribonucleotide - Google Patents
Modified oligodeoxyribonucleotideInfo
- Publication number
- JPH0892275A JPH0892275A JP7185115A JP18511595A JPH0892275A JP H0892275 A JPH0892275 A JP H0892275A JP 7185115 A JP7185115 A JP 7185115A JP 18511595 A JP18511595 A JP 18511595A JP H0892275 A JPH0892275 A JP H0892275A
- Authority
- JP
- Japan
- Prior art keywords
- dbp
- meoph
- group
- hhcoo
- hhco
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 108091034117 Oligonucleotide Proteins 0.000 title claims abstract description 42
- 229940124276 oligodeoxyribonucleotide Drugs 0.000 title claims abstract description 39
- 150000001875 compounds Chemical class 0.000 claims abstract description 188
- 150000005690 diesters Chemical class 0.000 claims abstract description 20
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 9
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 8
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 7
- 150000004713 phosphodiesters Chemical group 0.000 claims abstract description 7
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 claims abstract description 7
- 208000030507 AIDS Diseases 0.000 claims abstract description 5
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 4
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 3
- -1 anthraquinonyl group Chemical group 0.000 claims description 720
- 238000000034 method Methods 0.000 claims description 58
- 239000003795 chemical substances by application Substances 0.000 claims description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 24
- 125000001424 substituent group Chemical group 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 20
- 229910052739 hydrogen Inorganic materials 0.000 claims description 20
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 19
- 239000005547 deoxyribonucleotide Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- YACKEPLHDIMKIO-UHFFFAOYSA-N methylphosphonic acid Chemical compound CP(O)(O)=O YACKEPLHDIMKIO-UHFFFAOYSA-N 0.000 claims description 13
- 230000009021 linear effect Effects 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 11
- MHDVGSVTJDSBDK-UHFFFAOYSA-N dibenzyl ether Chemical group C=1C=CC=CC=1COCC1=CC=CC=C1 MHDVGSVTJDSBDK-UHFFFAOYSA-N 0.000 claims description 9
- 150000003839 salts Chemical class 0.000 claims description 9
- UYTPUPDQBNUYGX-UHFFFAOYSA-N Guanine Natural products O=C1NC(N)=NC2=C1N=CN2 UYTPUPDQBNUYGX-UHFFFAOYSA-N 0.000 claims description 7
- RWQNBRDOKXIBIV-UHFFFAOYSA-N Thymine Natural products CC1=CNC(=O)NC1=O RWQNBRDOKXIBIV-UHFFFAOYSA-N 0.000 claims description 7
- OPTASPLRGRRNAP-UHFFFAOYSA-N cytosine Natural products NC=1C=CNC(=O)N=1 OPTASPLRGRRNAP-UHFFFAOYSA-N 0.000 claims description 7
- ZDSRFXVZVHSYMA-CMOCDZPBSA-N (2s)-2-[[(2s)-2-[[(2s)-2-[[(2s)-2-amino-3-(4-hydroxyphenyl)propanoyl]amino]-3-(4-hydroxyphenyl)propanoyl]amino]-4-carboxybutanoyl]amino]pentanedioic acid Chemical compound C([C@H](N)C(=O)N[C@@H](CC=1C=CC(O)=CC=1)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](CCC(O)=O)C(O)=O)C1=CC=C(O)C=C1 ZDSRFXVZVHSYMA-CMOCDZPBSA-N 0.000 claims description 6
- 108010068794 tyrosyl-tyrosyl-glutamyl-glutamic acid Proteins 0.000 claims description 6
- 229930024421 Adenine Natural products 0.000 claims description 5
- 229960000643 adenine Drugs 0.000 claims description 5
- 229940104302 cytosine Drugs 0.000 claims description 5
- 229940113082 thymine Drugs 0.000 claims description 5
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 claims description 3
- 125000001834 xanthenyl group Chemical group C1=CC=CC=2OC3=CC=CC=C3C(C12)* 0.000 claims description 3
- 239000004480 active ingredient Substances 0.000 claims description 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 1
- 239000005289 controlled pore glass Substances 0.000 abstract description 62
- 239000002773 nucleotide Substances 0.000 abstract description 34
- 125000003729 nucleotide group Chemical group 0.000 abstract description 34
- 125000006239 protecting group Chemical group 0.000 abstract description 20
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract description 11
- 125000003277 amino group Chemical group 0.000 abstract description 9
- 230000000694 effects Effects 0.000 abstract description 9
- 125000002252 acyl group Chemical group 0.000 abstract description 4
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 4
- 241000725303 Human immunodeficiency virus Species 0.000 abstract description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 abstract description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 346
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 318
- 239000000243 solution Substances 0.000 description 94
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 93
- 238000006243 chemical reaction Methods 0.000 description 93
- 229910018557 Si O Inorganic materials 0.000 description 80
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 239000002904 solvent Substances 0.000 description 71
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 61
- 208000031882 Hereditary hyperferritinemia-cataract syndrome Diseases 0.000 description 60
- 208000027211 hereditary hyperferritinemia with congenital cataracts Diseases 0.000 description 60
- 208000014414 hyperferritinemia-cataract syndrome Diseases 0.000 description 60
- PXHVJJICTQNCMI-UHFFFAOYSA-N nickel Substances [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 60
- VMYREBYTVVSDDK-FQEVSTJZSA-N (3s)-3-(naphthalen-2-ylsulfonylamino)-4-oxo-4-(2-phenylethylamino)butanoic acid Chemical compound O=C([C@@H](NS(=O)(=O)C=1C=C2C=CC=CC2=CC=1)CC(=O)O)NCCC1=CC=CC=C1 VMYREBYTVVSDDK-FQEVSTJZSA-N 0.000 description 54
- 239000002585 base Substances 0.000 description 49
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 48
- 239000003153 chemical reaction reagent Substances 0.000 description 48
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 42
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 37
- 239000000126 substance Substances 0.000 description 37
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- 108020004414 DNA Proteins 0.000 description 33
- AVBGNFCMKJOFIN-UHFFFAOYSA-N triethylammonium acetate Chemical compound CC(O)=O.CCN(CC)CC AVBGNFCMKJOFIN-UHFFFAOYSA-N 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
- AUZONCFQVSMFAP-UHFFFAOYSA-N disulfiram Chemical compound CCN(CC)C(=S)SSC(=S)N(CC)CC AUZONCFQVSMFAP-UHFFFAOYSA-N 0.000 description 30
- 239000000203 mixture Substances 0.000 description 30
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 30
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 30
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
- 230000008878 coupling Effects 0.000 description 27
- 238000010168 coupling process Methods 0.000 description 27
- 238000005859 coupling reaction Methods 0.000 description 27
- 238000000746 purification Methods 0.000 description 26
- 230000035484 reaction time Effects 0.000 description 26
- 238000004007 reversed phase HPLC Methods 0.000 description 26
- 239000002777 nucleoside Substances 0.000 description 25
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 24
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 24
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 24
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 24
- 230000002829 reductive effect Effects 0.000 description 22
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 239000011630 iodine Substances 0.000 description 20
- 229910052740 iodine Inorganic materials 0.000 description 20
- 238000007254 oxidation reaction Methods 0.000 description 20
- 230000001590 oxidative effect Effects 0.000 description 20
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 18
- 239000012071 phase Substances 0.000 description 18
- 150000008282 halocarbons Chemical class 0.000 description 17
- 239000007858 starting material Substances 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- IQFYYKKMVGJFEH-XLPZGREQSA-N Thymidine Chemical compound O=C1NC(=O)C(C)=CN1[C@@H]1O[C@H](CO)[C@@H](O)C1 IQFYYKKMVGJFEH-XLPZGREQSA-N 0.000 description 14
- 150000003833 nucleoside derivatives Chemical class 0.000 description 14
- 239000007800 oxidant agent Substances 0.000 description 14
- 150000001408 amides Chemical class 0.000 description 13
- 150000002825 nitriles Chemical class 0.000 description 13
- HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 12
- 241000713772 Human immunodeficiency virus 1 Species 0.000 description 12
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 12
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 12
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical compound OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 12
- 230000015572 biosynthetic process Effects 0.000 description 12
- 150000002170 ethers Chemical class 0.000 description 12
- 150000003462 sulfoxides Chemical class 0.000 description 12
- 238000003786 synthesis reaction Methods 0.000 description 12
- 239000003643 water by type Substances 0.000 description 12
- 229910019142 PO4 Inorganic materials 0.000 description 11
- 239000003054 catalyst Substances 0.000 description 11
- 238000004587 chromatography analysis Methods 0.000 description 11
- 238000004440 column chromatography Methods 0.000 description 11
- 238000001914 filtration Methods 0.000 description 11
- 239000010452 phosphate Substances 0.000 description 11
- 230000002441 reversible effect Effects 0.000 description 11
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 10
- 150000002576 ketones Chemical class 0.000 description 10
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 10
- 238000005406 washing Methods 0.000 description 10
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 150000002148 esters Chemical class 0.000 description 9
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 9
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 9
- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 8
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 8
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 8
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 8
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 8
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 238000007796 conventional method Methods 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- PHTQWCKDNZKARW-UHFFFAOYSA-N isoamylol Chemical compound CC(C)CCO PHTQWCKDNZKARW-UHFFFAOYSA-N 0.000 description 8
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 8
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 8
- 125000003835 nucleoside group Chemical group 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- 239000003960 organic solvent Substances 0.000 description 8
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 238000001953 recrystallisation Methods 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- 238000011282 treatment Methods 0.000 description 8
- DWRXFEITVBNRMK-UHFFFAOYSA-N Beta-D-1-Arabinofuranosylthymine Natural products O=C1NC(=O)C(C)=CN1C1C(O)C(O)C(CO)O1 DWRXFEITVBNRMK-UHFFFAOYSA-N 0.000 description 7
- QOSSAOTZNIDXMA-UHFFFAOYSA-N Dicylcohexylcarbodiimide Chemical compound C1CCCCC1N=C=NC1CCCCC1 QOSSAOTZNIDXMA-UHFFFAOYSA-N 0.000 description 7
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 150000004982 aromatic amines Chemical class 0.000 description 7
- IQFYYKKMVGJFEH-UHFFFAOYSA-N beta-L-thymidine Natural products O=C1NC(=O)C(C)=CN1C1OC(CO)C(O)C1 IQFYYKKMVGJFEH-UHFFFAOYSA-N 0.000 description 7
- XMPZTFVPEKAKFH-UHFFFAOYSA-P ceric ammonium nitrate Chemical compound [NH4+].[NH4+].[Ce+4].[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O.[O-][N+]([O-])=O XMPZTFVPEKAKFH-UHFFFAOYSA-P 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 7
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical class OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 7
- 238000005987 sulfurization reaction Methods 0.000 description 7
- 229940104230 thymidine Drugs 0.000 description 7
- 239000008096 xylene Substances 0.000 description 7
- RBBIKFDLPCEOTF-UHFFFAOYSA-N 2,3,4-tri(propan-2-yl)benzenesulfonic acid Chemical compound CC(C)C1=CC=C(S(O)(=O)=O)C(C(C)C)=C1C(C)C RBBIKFDLPCEOTF-UHFFFAOYSA-N 0.000 description 6
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- 230000002378 acidificating effect Effects 0.000 description 6
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 6
- WQOXQRCZOLPYPM-UHFFFAOYSA-N dimethyl disulfide Chemical compound CSSC WQOXQRCZOLPYPM-UHFFFAOYSA-N 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000009472 formulation Methods 0.000 description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
- 239000012442 inert solvent Substances 0.000 description 6
- NUJOXMJBOLGQSY-UHFFFAOYSA-N manganese dioxide Chemical compound O=[Mn]=O NUJOXMJBOLGQSY-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 150000007530 organic bases Chemical class 0.000 description 6
- CTSLXHKWHWQRSH-UHFFFAOYSA-N oxalyl chloride Chemical compound ClC(=O)C(Cl)=O CTSLXHKWHWQRSH-UHFFFAOYSA-N 0.000 description 6
- 230000003647 oxidation Effects 0.000 description 6
- 238000012856 packing Methods 0.000 description 6
- IZUPBVBPLAPZRR-UHFFFAOYSA-N pentachlorophenol Chemical compound OC1=C(Cl)C(Cl)=C(Cl)C(Cl)=C1Cl IZUPBVBPLAPZRR-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 150000008300 phosphoramidites Chemical class 0.000 description 6
- USHAGKDGDHPEEY-UHFFFAOYSA-L potassium persulfate Chemical compound [K+].[K+].[O-]S(=O)(=O)OOS([O-])(=O)=O USHAGKDGDHPEEY-UHFFFAOYSA-L 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 229910052708 sodium Inorganic materials 0.000 description 6
- CHQMHPLRPQMAMX-UHFFFAOYSA-L sodium persulfate Substances [Na+].[Na+].[O-]S(=O)(=O)OOS([O-])(=O)=O CHQMHPLRPQMAMX-UHFFFAOYSA-L 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- DLYUQMMRRRQYAE-UHFFFAOYSA-N tetraphosphorus decaoxide Chemical compound O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 6
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- LCPVQAHEFVXVKT-UHFFFAOYSA-N 2-(2,4-difluorophenoxy)pyridin-3-amine Chemical compound NC1=CC=CN=C1OC1=CC=C(F)C=C1F LCPVQAHEFVXVKT-UHFFFAOYSA-N 0.000 description 5
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- 125000005036 alkoxyphenyl group Chemical group 0.000 description 1
- 125000005037 alkyl phenyl group Chemical group 0.000 description 1
- VOZYXUHNEBULJT-UHFFFAOYSA-N aluminum oxygen(2-) rhodium(3+) Chemical compound [O--].[O--].[O--].[Al+3].[Rh+3] VOZYXUHNEBULJT-UHFFFAOYSA-N 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 150000003927 aminopyridines Chemical class 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 230000003698 anagen phase Effects 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 125000000748 anthracen-2-yl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C([H])=C([*])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 125000002178 anthracenyl group Chemical group C1(=CC=CC2=CC3=CC=CC=C3C=C12)* 0.000 description 1
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- HKVFISRIUUGTIB-UHFFFAOYSA-O azanium;cerium;nitrate Chemical compound [NH4+].[Ce].[O-][N+]([O-])=O HKVFISRIUUGTIB-UHFFFAOYSA-O 0.000 description 1
- 125000005603 azodicarboxylic group Chemical group 0.000 description 1
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Inorganic materials [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 1
- HSDAJNMJOMSNEV-UHFFFAOYSA-N benzyl chloroformate Chemical compound ClC(=O)OCC1=CC=CC=C1 HSDAJNMJOMSNEV-UHFFFAOYSA-N 0.000 description 1
- 125000000649 benzylidene group Chemical group [H]C(=[*])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000001584 benzyloxycarbonyl group Chemical group C(=O)(OCC1=CC=CC=C1)* 0.000 description 1
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- VJVOPINBJQWMNY-UHFFFAOYSA-N butanedioic acid;ethane-1,2-diol Chemical compound OCCO.OC(=O)CCC(O)=O VJVOPINBJQWMNY-UHFFFAOYSA-N 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 230000010261 cell growth Effects 0.000 description 1
- 230000004663 cell proliferation Effects 0.000 description 1
- 239000006285 cell suspension Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000010980 cellulose Nutrition 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000007810 chemical reaction solvent Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- IDNJBJJSMDYULP-UHFFFAOYSA-N chlorophosphonamidous acid Chemical compound NP(O)Cl IDNJBJJSMDYULP-UHFFFAOYSA-N 0.000 description 1
- 229940075614 colloidal silicon dioxide Drugs 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- 229940126214 compound 3 Drugs 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 239000002385 cottonseed oil Substances 0.000 description 1
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000012351 deprotecting agent Substances 0.000 description 1
- 238000010511 deprotection reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- 239000012973 diazabicyclooctane Substances 0.000 description 1
- WGLUMOCWFMKWIL-UHFFFAOYSA-N dichloromethane;methanol Chemical compound OC.ClCCl WGLUMOCWFMKWIL-UHFFFAOYSA-N 0.000 description 1
- 239000012470 diluted sample Substances 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 125000005982 diphenylmethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 239000003480 eluent Substances 0.000 description 1
- 238000010828 elution Methods 0.000 description 1
- KFSUNTUMPUWCMW-UHFFFAOYSA-N ethanol;perchloric acid Chemical compound CCO.OCl(=O)(=O)=O KFSUNTUMPUWCMW-UHFFFAOYSA-N 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000001747 exhibiting effect Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000012091 fetal bovine serum Substances 0.000 description 1
- 125000004175 fluorobenzyl group Chemical group 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000007903 gelatin capsule Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 230000012010 growth Effects 0.000 description 1
- 125000004993 haloalkoxycarbonyl group Chemical group 0.000 description 1
- 239000007902 hard capsule Substances 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 125000002346 iodo group Chemical group I* 0.000 description 1
- 125000006303 iodophenyl group Chemical group 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 1
- 229910052808 lithium carbonate Inorganic materials 0.000 description 1
- 231100000053 low toxicity Toxicity 0.000 description 1
- UKVIEHSSVKSQBA-UHFFFAOYSA-N methane;palladium Chemical compound C.[Pd] UKVIEHSSVKSQBA-UHFFFAOYSA-N 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 description 1
- 229940016286 microcrystalline cellulose Drugs 0.000 description 1
- 235000019813 microcrystalline cellulose Nutrition 0.000 description 1
- 239000008108 microcrystalline cellulose Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
- 235000008390 olive oil Nutrition 0.000 description 1
- BJLZAAWLLPMZQR-UHFFFAOYSA-N oxo-di(propan-2-yloxy)phosphanium Chemical compound CC(C)O[P+](=O)OC(C)C BJLZAAWLLPMZQR-UHFFFAOYSA-N 0.000 description 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 description 1
- OTCVAHKKMMUFAY-UHFFFAOYSA-N oxosilver Chemical class [Ag]=O OTCVAHKKMMUFAY-UHFFFAOYSA-N 0.000 description 1
- 230000036961 partial effect Effects 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- RGSFGYAAUTVSQA-UHFFFAOYSA-N pentamethylene Natural products C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 1
- 125000004817 pentamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 230000000737 periodic effect Effects 0.000 description 1
- 125000001792 phenanthrenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C=CC12)* 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- UYWQUFXKFGHYNT-UHFFFAOYSA-N phenylmethyl ester of formic acid Natural products O=COCC1=CC=CC=C1 UYWQUFXKFGHYNT-UHFFFAOYSA-N 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 150000003003 phosphines Chemical class 0.000 description 1
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
- 229910003446 platinum oxide Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 230000000069 prophylactic effect Effects 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 125000001742 pyren-1-yl group Chemical group [H]C1=C([H])C2=C([H])C([H])=C3C(*)=C([H])C([H])=C4C([H])=C([H])C(=C1[H])C2=C34 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000006722 reduction reaction Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004366 reverse phase liquid chromatography Methods 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 125000003808 silyl group Chemical class [H][Si]([H])([H])[*] 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 230000001954 sterilising effect Effects 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003900 succinic acid esters Chemical class 0.000 description 1
- YSWKHCWXOYCOSF-UHFFFAOYSA-N tert-butyl chlorite Chemical compound CC(C)(C)OCl=O YSWKHCWXOYCOSF-UHFFFAOYSA-N 0.000 description 1
- IXZDIALLLMRYOU-UHFFFAOYSA-N tert-butyl hypochlorite Chemical compound CC(C)(C)OCl IXZDIALLLMRYOU-UHFFFAOYSA-N 0.000 description 1
- BCNZYOJHNLTNEZ-UHFFFAOYSA-N tert-butyldimethylsilyl chloride Chemical compound CC(C)(C)[Si](C)(C)Cl BCNZYOJHNLTNEZ-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 230000001225 therapeutic effect Effects 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 125000005039 triarylmethyl group Chemical group 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- FEQPHYCEZKWPNE-UHFFFAOYSA-K trichlororhodium;triphenylphosphane Chemical compound Cl[Rh](Cl)Cl.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 FEQPHYCEZKWPNE-UHFFFAOYSA-K 0.000 description 1
- YFWYBODXCVNXNZ-UHFFFAOYSA-N tris(1h-1,2,4-triazol-5-yl) phosphite Chemical compound N1=CNN=C1OP(OC1=NNC=N1)OC=1N=CNN=1 YFWYBODXCVNXNZ-UHFFFAOYSA-N 0.000 description 1
- JABYJIQOLGWMQW-UHFFFAOYSA-N undec-4-ene Chemical compound CCCCCCC=CCCC JABYJIQOLGWMQW-UHFFFAOYSA-N 0.000 description 1
- 230000003612 virological effect Effects 0.000 description 1
- 239000008215 water for injection Substances 0.000 description 1
- 229940102001 zinc bromide Drugs 0.000 description 1
Classifications
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups
Landscapes
- Saccharide Compounds (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
Description
【０００１】[0001]
【発明の属する技術分野】本発明は、優れた抗エイズウ
イルス作用を有する新規な修飾オリゴデオキシリボヌク
レオチドに関する。TECHNICAL FIELD The present invention relates to a novel modified oligodeoxyribonucleotide having an excellent anti-AIDS virus activity.
【０００２】[0002]
【従来の技術】ある遺伝子に相補的な配列を有するオリ
ゴデオキシリボヌクレオチド（アンチセンスオリゴデオ
キシリボヌクレオチド）はその遺伝子の機能発現を阻害
することが知られている。また、ウイルス遺伝子または
オンコジーンに対するアンチセンスオリゴデオキシリボ
ヌクレオチドはその遺伝子の機能を阻害することによ
り、それぞれウイルスの複製または細胞の増殖を阻害し
うることが報告されている(P.C. Zamecnik, M.L. Steph
enson, Proc. Natl. Acad. Sci. USA, 75巻、１号、２
８０頁（１９７８）およびP.C. Zamecnik, J. Goodchi
ld, Y. Taguchi,Sarin, Proc. Natl. Acad. Sci. US
A, 83巻、6 号、4143頁（1986）) 。2. Description of the Related Art It is known that oligodeoxyribonucleotides (antisense oligodeoxyribonucleotides) having a sequence complementary to a gene inhibit the functional expression of the gene. It has also been reported that antisense oligodeoxyribonucleotides against viral genes or oncogenes can inhibit viral replication or cell proliferation, respectively, by inhibiting the function of that gene (PC Zamecnik, ML Steph
enson, Proc. Natl. Acad. Sci. USA, Volume 75, Issue 1, 2
Page 80 (1978) and PC Zamecnik, J. Goodchi.
ld, Y. Taguchi, Sarin, Proc. Natl. Acad. Sci. US
A, Vol. 83, No. 6, p. 4143 (1986)).
【０００３】[0003]
【発明が解決しようとする課題】ここで、これらアンチ
センスオリゴデオキシリボヌクレオチドが、その作用を
示すためには、生体内で標的とするＲＮＡ若しくはＤＮ
Ａと安定なハイブリッドを形成しなくてはならず、その
ためには、少なくとも１５ヌクレオチド程度以上の長さ
のオリゴデオキシリボヌクレオチドであることが必要と
されていた。一般に、長さが１５ヌクレオチド程度のも
のは、合成コスト及び血液中における安定性の問題によ
り、その実用化が困難である。また、これらアンチセン
スオリゴデオキシリボヌクレオチドによるウイルスの複
製または細胞の増殖阻害活性も十分満足するものとはい
えず、さらに、宿主の正常細胞に対する毒性も比較的高
かった。Here, in order for these antisense oligodeoxyribonucleotides to exhibit their action, RNA or DN targeted in vivo is required.
It has to form a stable hybrid with A, and for that purpose, oligodeoxyribonucleotide having a length of at least about 15 nucleotides or more was required. In general, those having a length of about 15 nucleotides are difficult to put into practical use due to problems of synthesis cost and stability in blood. In addition, the activity of inhibiting virus replication or cell growth by these antisense oligodeoxyribonucleotides cannot be said to be sufficiently satisfactory, and the toxicity to host normal cells was relatively high.
【０００４】[0004]
【課題を解決するための手段】本発明者らは，これまで
特異的な阻害活性を発揮しえないと考えられていた鎖長
の短いオリゴデオキシリボヌクレオチドについて，部分
的にホスホジエステル基がホスホロチオエート型ジエス
テル基、メチルホスホネート型ジエステル基あるいはメ
トキシエチルアミノホスフェート型ジエステル基に変換
され、かつ、種々の塩基配列並びに5'末端及び3'末端側
に種々の修飾基を有する該ヌクレオチドを鋭意検討した
結果，一定の塩基配列からなる修飾オリゴデオキシリボ
ヌクレオチドは，顕著に高い抗エイズウイルス作用を有
し，血液中での安定性が増大し、宿主の正常細胞に対す
る毒性は低く、かつ、合成も比較的容易で実用性がある
ことを見出し、本発明を完成するに至った。Means for Solving the Problems With respect to oligodeoxyribonucleotides having a short chain length, which have hitherto been considered to be incapable of exhibiting a specific inhibitory activity, the phosphodiester groups are partially phosphorothioate type. A diester group, a methylphosphonate type diester group or a methoxyethylaminophosphate type diester group, and as a result of diligent examination of the nucleotide having various base sequences and various modifying groups on the 5′-terminal and 3′-terminal side, A modified oligodeoxyribonucleotide consisting of a fixed nucleotide sequence has a remarkably high anti-AIDS virus activity, increased stability in blood, low toxicity to normal cells of the host, and relatively easy synthesis. The inventors have found that they have practicality and have completed the present invention.
【０００５】本発明の新規な修飾オリゴデオキシリボヌ
クレオチドは、一般式The novel modified oligodeoxyribonucleotides of the present invention have the general formula
【０００６】[0006]
【化２】 [Chemical 2]
【０００７】を有する。Having
【０００８】上記式（１）において、ＱはＲ1 Ｒ2 Ｒ3
Ｚ基（式中、Ｒ1 、Ｒ2 及びＲ3 はそれぞれ独立に同一
又は異なって水素原子、炭素数１乃至４個のアルキル
基、置換基を有していてもよいアリール基又は置換基を
有していてもよいアンスラキノニル基を示し、ＺはＣ又
はＳｉを示すか、あるいは、Ｒ2 、Ｒ3 及びＺが一緒に
なってフルオレニル基又はキサンテニル基を示す。）を
示し、Ｒ4 は水素原子、置換基を有していてもよい炭素
数１乃至４個のアルキル基、置換基を有していてもよい
アリール基又は置換基を有していてもよいアラルキル
基、Ｙ1 、Ｙ3 及びＹ4 は同一又は異なってＯ，Ｓ又は
ＮＨを示し、Ｙ2 はＯ，Ｓ，ＮＨ，炭素数１乃至４個の
アルキレン基又はフェニレン基を示し、Ｘは水酸基で置
換されていてもよい直鎖又は分枝鎖の炭素数１乃至１０
個のアルキレン基を示し、ｍ、ｎは同一又は異なって０
乃至１０の整数を示し、Ｂは鎖長が３乃至９の部分的に
ホスホジエステル基がホスホロチオエート型ジエステル
基（In the above formula (1), Q is R 1 R 2 R 3
Z group (in the formula, R 1 , R 2 and R 3 are independently the same or different and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, an aryl group which may have a substituent or a substituent) Represents an anthraquinonyl group which may have, Z represents C or Si, or R 2 , R 3 and Z together represent a fluorenyl group or a xanthenyl group), and R 4 Is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms which may have a substituent, an aryl group which may have a substituent or an aralkyl group which may have a substituent, Y 1 , Y 3 and Y 4 are the same or different and each represents O, S or NH, Y 2 represents O, S, NH, an alkylene group having 1 to 4 carbon atoms or a phenylene group, and X is substituted with a hydroxyl group. Good straight or branched chain carbon atoms 1 to 10
Represents an alkylene group, and m and n are the same or different and are 0
B is an integer of 10 to 10, and B is a partially phosphodiester group having a chain length of 3 to 9 and a phosphorothioate type diester group (
【０００９】[0009]
【化３】 [Chemical 3]
【００１０】）、メチルホスホネート型ジエステル基（), A methylphosphonate type diester group (
【００１１】[0011]
【化４】 [Chemical 4]
【００１２】）あるいはメトキシエチルアミノホスフェ
ート型ジエステル基（) Or a methoxyethylaminophosphate type diester group (
【００１３】[0013]
【化５】 [Chemical 5]
【００１４】）に変換されたオリゴデオキシリボヌクレ
オチド（ＯＤＮ）を示す。但し、Ｂにおいて、各オリゴ
デオキシリボヌクレオチドの５’末端と３’末端の水酸
基は含まない。3) shows an oligodeoxyribonucleotide (ODN) converted into However, in B, the hydroxyl groups at the 5'end and 3'end of each oligodeoxyribonucleotide are not included.
【００１５】前記式（１）において、Ｑ基のＲ1 、Ｒ2
及びＲ3 の炭素数１乃至４個のアルキル基としては、例
えば、メチル、エチル、n-プロピル、イソプロピル、n-
ブチル、イソブチル、s-ブチル、t-ブチルがあげられ、
好適にはｔ−ブチルである。前記式（１）において、Ｑ
基のＲ1 、Ｒ2 及びＲ3 の置換基を有していてもよいア
リール基としては、例えば、フェニル、４−メチルフェ
ニル、４−ｔ−ブチルフェニル、２−フェニルフェニ
ル、４−フェニルフェニル、４−フルオロフェニル、２
−クロロフェニル、４−クロロフェニル、４−ブロモフ
ェニル、４−ヨードフェニル、２，４−ジフルオロフェ
ニル、４ーニトロフェニル、４−ｔ−ブトキシフェニ
ル、４−メトキシフェニル、４−エトキシフェニル、３
−フェノキシフェニル、４−フェノキシフェニル、２−
ベンジルオキシフェニル、４−ベンジルオキシフェニ
ル、３，４−（ジベンジルオキシ）フェニル、３，５−
（ジベンジルオキシ）フェニル、３，５−ビス［３，５
−（ジベンジルオキシ）ベンジルオキシ］ベンジルオキ
シ、ナフタレン−１−イル、ナフタレン−２−イル、フ
ェナンスレン−４−イル、アントラセン−９−イル、ア
ントラセン−２−イル、ピレニル基があげられ、好適に
はフェニル、４−メトキシフェニル、３，４−（ジベン
ジルオキシ）フェニル、３，５−（ジベンジルオキシ）
フェニル、３，５−ビス［３，５−（ジベンジルオキ
シ）ベンジルオキシ］ベンジルオキシ基である。In the above formula (1), R 1 and R 2 of the Q group are
And the alkyl group having 1 to 4 carbon atoms of R 3 includes, for example, methyl, ethyl, n-propyl, isopropyl, n-
Butyl, isobutyl, s-butyl, t-butyl,
It is preferably t-butyl. In the formula (1), Q
Examples of the aryl group which may have a substituent of R 1 , R 2 and R 3 of the group include, for example, phenyl, 4-methylphenyl, 4-t-butylphenyl, 2-phenylphenyl and 4-phenylphenyl. , 4-fluorophenyl, 2
-Chlorophenyl, 4-chlorophenyl, 4-bromophenyl, 4-iodophenyl, 2,4-difluorophenyl, 4-nitrophenyl, 4-t-butoxyphenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 3
-Phenoxyphenyl, 4-phenoxyphenyl, 2-
Benzyloxyphenyl, 4-benzyloxyphenyl, 3,4- (dibenzyloxy) phenyl, 3,5-
(Dibenzyloxy) phenyl, 3,5-bis [3,5
Examples include-(dibenzyloxy) benzyloxy] benzyloxy, naphthalen-1-yl, naphthalen-2-yl, phenanthren-4-yl, anthracen-9-yl, anthracen-2-yl and pyrenyl groups, and preferred Is phenyl, 4-methoxyphenyl, 3,4- (dibenzyloxy) phenyl, 3,5- (dibenzyloxy)
Phenyl and 3,5-bis [3,5- (dibenzyloxy) benzyloxy] benzyloxy groups.
【００１６】前記式（１）において、Ｑ基の置換基を有
していてもよいアントラキノニル基としては、例えば、
9,10- アントラキノン−１−イル、9,10- アントラキノ
ン−２−イル、9,10- アントラキノン−４−メチル−１
−イル、9,10- アントラキノン−５−メトキシ−１−イ
ル、9,10- アントラキノン−７−クロロ−１−イル、9,
10- アントラキノン−８−フルオロ−２−イル、9,10-
アントラキノン−６−エチル−２−イル、9,10- アント
ラキノン−８−エトキシ−２−イル、9,10- アントラキ
ノン−６−ヒドロキシ−１−イルがあげられ、好適には
無置換のものである。In the formula (1), examples of the anthraquinonyl group which may have a substituent of the Q group include:
9,10-anthraquinone-1-yl, 9,10-anthraquinone-2-yl, 9,10-anthraquinone-4-methyl-1
-Yl, 9,10-anthraquinone-5-methoxy-1-yl, 9,10-anthraquinone-7-chloro-1-yl, 9,
10- Anthraquinone-8-fluoro-2-yl, 9,10-
Examples thereof include anthraquinone-6-ethyl-2-yl, 9,10-anthraquinone-8-ethoxy-2-yl and 9,10-anthraquinone-6-hydroxy-1-yl, preferably unsubstituted. .
【００１７】前記式（１）において、Ｑ基のＲ2 、Ｒ3
及びＺが一緒になって形成するフルオレニル基又はキサ
ンテニル基としては、好適には、フルオレン−９−イ
ル、キサンテン−９−イルである。In the above formula (1), R 2 and R 3 of the Q group are
The fluorenyl group or xanthenyl group formed by Z and Z together is preferably fluoren-9-yl or xanthen-9-yl.
【００１８】前記式（１）において、Ｒ4 の置換基を有
していてもよい炭素数１乃至４個のアルキル基として
は、例えば、メチル、エチル、２−アミノエチル、２−
メトキシエチル、n-プロピル、イソプロピル、n-ブチ
ル、イソブチル、s-ブチル、t-ブチルがあげられ、好適
にはメチル、エチル、２−アミノエチル、２−メトキシ
エチル、n-プロピル基である。In the above formula (1), examples of the alkyl group having 1 to 4 carbon atoms which may have a substituent of R 4 include, for example, methyl, ethyl, 2-aminoethyl, 2-
Methoxyethyl, n-propyl, isopropyl, n-butyl, isobutyl, s-butyl, t-butyl can be mentioned, with preference given to methyl, ethyl, 2-aminoethyl, 2-methoxyethyl and n-propyl groups.
【００１９】前記式（１）において、Ｒ4 の置換基を有
していてもよいアリール基としては、例えば、フェニ
ル；２−メチルフェニル、３−エチルフェニル等のアル
キルフェニル；２−フルオロフェニル、２−クロロフェ
ニル、４−クロロフェニル、２−ブロモフェニル、２−
ヨードフェニル等のハロゲン化フェニル；２−ニトロフ
ェニル、４−ニトロフェニル等のニトロフェニル；４−
メトキシフェニル、４−エトキシフェニル等のアルコキ
シフェニル、４−メチルチオフェニル、４−エチルチオ
フェニル等のアルキルチオフェニル、ナフチル、フェナ
ンスレニル、アントラセニル、ピレニル基があげられ、
好適には無置換フェニル、ハロゲン化フェニル、ニトロ
フェニルである。In the above formula (1), examples of the aryl group which may have a substituent of R 4 include phenyl; alkylphenyl such as 2-methylphenyl and 3-ethylphenyl; 2-fluorophenyl, 2-chlorophenyl, 4-chlorophenyl, 2-bromophenyl, 2-
Halogenated phenyl such as iodophenyl; Nitrophenyl such as 2-nitrophenyl and 4-nitrophenyl; 4-
Examples include alkoxyphenyl such as methoxyphenyl and 4-ethoxyphenyl, alkylthiophenyl such as 4-methylthiophenyl and 4-ethylthiophenyl, naphthyl, phenanthrenyl, anthracenyl and pyrenyl groups.
Preferred are unsubstituted phenyl, halogenated phenyl, and nitrophenyl.
【００２０】前記式（１）において、Ｒ4 の置換基を有
していてもよいアラルキル基としては、例えば、ベンジ
ル、メチルベンジル、エチルベンジル、メトキシベンジ
ル、エトキシベンジル、フルオロベンジル、クロロベン
ジル、ブロモベンジル、クロロナフチルメチル、インデ
ニルメチル、フェナンスレニルメチル、アントラセニル
メチル、ジフェニルメチル、トリフェニルメチル、1-フ
ェネチル、2-フェネチル、2,2-ジフェニルエチル、2,2,
2-トリフェニルエチル、3,3,3,- トリフェニルプロピ
ル、1-ナフチルエチル、2-ナフチルエチル、1-フェニル
プロピル、2-フェニルプロピル、3-フェニルプロピル、
1-ナフチルプロピル、2-ナフチルプロピル、3-ナフチル
プロピル、1-フェニルブチル、2-フェニルブチル、3-フ
ェニルブチル、4-フェニルブチル、1-ナフチルブチル、
2-ナフチルブチル、3-ナフチルブチル、4-ナフチルブチ
ル、1-フェニルペンチル、2-フェニルペンチル、3-フェ
ニルペンチル、4-フェニルペンチル、5-フェニルペンチ
ル、1-ナフチルペンチル、2-ナフチルペンチル、3-ナフ
チルペンチル、4-ナフチルペンチル、5-ナフチルペンチ
ル、1-フェニルヘキシル、2-フェニルヘキシル、3-フェ
ニルヘキシル、4-フェニルヘキシル、5-フェニルヘキシ
ル、6-フェニルヘキシル、1-ナフチルヘキシル、2-ナフ
チルヘキシル、3-ナフチルヘキシル、4-ナフチルヘキシ
ル、5-ナフチルヘキシル、6-ナフチルヘキシルがあげら
れ、好適には無置換のベンジル又は2-フェネチルであ
る。In the above formula (1), the aralkyl group which may have a substituent for R 4 is, for example, benzyl, methylbenzyl, ethylbenzyl, methoxybenzyl, ethoxybenzyl, fluorobenzyl, chlorobenzyl or bromo. Benzyl, chloronaphthylmethyl, indenylmethyl, phenanthrenylmethyl, anthracenylmethyl, diphenylmethyl, triphenylmethyl, 1-phenethyl, 2-phenethyl, 2,2-diphenylethyl, 2,2,
2-triphenylethyl, 3,3,3, -triphenylpropyl, 1-naphthylethyl, 2-naphthylethyl, 1-phenylpropyl, 2-phenylpropyl, 3-phenylpropyl,
1-naphthylpropyl, 2-naphthylpropyl, 3-naphthylpropyl, 1-phenylbutyl, 2-phenylbutyl, 3-phenylbutyl, 4-phenylbutyl, 1-naphthylbutyl,
2-naphthylbutyl, 3-naphthylbutyl, 4-naphthylbutyl, 1-phenylpentyl, 2-phenylpentyl, 3-phenylpentyl, 4-phenylpentyl, 5-phenylpentyl, 1-naphthylpentyl, 2-naphthylpentyl, 3-naphthylpentyl, 4-naphthylpentyl, 5-naphthylpentyl, 1-phenylhexyl, 2-phenylhexyl, 3-phenylhexyl, 4-phenylhexyl, 5-phenylhexyl, 6-phenylhexyl, 1-naphthylhexyl, Examples thereof include 2-naphthylhexyl, 3-naphthylhexyl, 4-naphthylhexyl, 5-naphthylhexyl and 6-naphthylhexyl, and unsubstituted benzyl or 2-phenethyl is preferable.
【００２１】前記式（１）において、Ｙ2 の炭素数１乃
至４個のアルキレンとしては、メチレン、エチレン、プ
ロピレン、テトラメチレン、ペンタメチレンがあげら
れ、好適にはメチレンである。In the above formula (1), the alkylene having 1 to 4 carbon atoms for Y 2 includes methylene, ethylene, propylene, tetramethylene and pentamethylene, and preferably methylene.
【００２２】前記式（１）において、Ｙ1 、Ｙ3 及びＹ
4 は、好適には酸素原子である。In the above formula (1), Y 1 , Y 3 and Y
4 is preferably an oxygen atom.
【００２３】前記式（１）において、Ｙ2 は、好適には
酸素又は硫黄原子である。In the above formula (1), Y 2 is preferably an oxygen or sulfur atom.
【００２４】前記式（１）において、Ｑ基のＺは、好適
には炭素原子である。In the above formula (1), Z in the Q group is preferably a carbon atom.
【００２５】前記式（１）において、Ｘの水酸基で置換
されていてもよい直鎖又は分枝鎖の炭素数１乃至１０個
のアルキレン基としては、例えば、メチレン、メチルメ
チレン、エチレン、プロピレン、テトラメチレン、メチ
ルエチレン、1-メチルトリメチレン、2-メチルトリメチ
レン、2-メチルテトラメチレン、3-メチルトリメチレ
ン、ペンタメチレン、ヘキサメチレン、へプタメチレ
ン、オクタメチレン、ノナメチレン、デカメチレン、2-
ヒドロキシトリメチレン、2-ヒドロキシテトラメチレン
があげられ、好適にはメチレン、メチルメチレン、エチ
レン、プロピレン、メチルエチレン基である。In the above formula (1), examples of the linear or branched alkylene group having 1 to 10 carbon atoms which may be substituted with the hydroxyl group of X include, for example, methylene, methylmethylene, ethylene, propylene, Tetramethylene, methylethylene, 1-methyltrimethylene, 2-methyltrimethylene, 2-methyltetramethylene, 3-methyltrimethylene, pentamethylene, hexamethylene, heptamethylene, octamethylene, nonamethylene, decamethylene, 2-
Examples thereof include hydroxytrimethylene and 2-hydroxytetramethylene, with methylene, methylmethylene, ethylene, propylene and methylethylene groups being preferred.
【００２６】前記式（１）において、ｍ、ｎは、好適に
は０乃至６であり、さらに、ｍについては０乃至４であ
る。In the above formula (1), m and n are preferably 0 to 6, and m is 0 to 4.
【００２７】前記式（１）において、Ｂのオリゴデオキ
シリボヌクレオチドのうち、好適なものとしては、鎖長
が４乃至８のものであり、さらに好適なものとしては、
鎖長が５乃至６のものである。In the above formula (1), among the oligodeoxyribonucleotides of B, preferable ones are those having a chain length of 4 to 8, and more preferable ones are:
It has a chain length of 5 to 6.
【００２８】さらにまた、好適なものとしては下記Ａ群
に記載のものであり、より好適なものとしては下記Ｂ群
に記載のものであり、さらに好適なものとしては下記Ｃ
群に記載のものであり、よりさらに好適なものとしては
下記Ｄ群に記載のものであり、最も好適には下記Ｅ群に
記載のものである。Further, preferred are those described in the following group A, more preferred are those described in the following group B, and more preferred are those described below in C.
Group D, more preferably those described in Group D below, and most preferably those described in Group E below.
【００２９】なお、Ａ、Ｂ、Ｃ、Ｄ及びＥ群中、Ａはア
デニンデオキシリボヌクレオチド、Ｇはグアニンデオキ
シリボヌクレオチド、Ｃはシトシンデオキシリボヌクレ
オチド、Ｔはチミンデオキシリボヌクレオチド、ｍＣは
５−メチルシトシンデオキシリボヌクレオチド又はｍＧ
はＯ6 −メチルグアニンデオキシリボヌクレオチドを示
す。また、左端が５’末端であり、右端が３’末端であ
る。但し、各オリゴデオキシリボヌクレオチドの５’末
端と３’末端の水酸基は含まない。さらに、ｅ、ｆ又は
ｇがＡ、Ｇ、Ｃ又はＴの間に挿入されている場合は、ホ
スホジエステル基がホスホロチオエート型ジエステル基
（ｅ）、メチルホスホネート型ジエステル基（ｆ）ある
いはメトキシエチルアミノホスフェート型ジエステル基
（ｇ）に変換されていることを示す。In the groups A, B, C, D and E, A is adenine deoxyribonucleotide, G is guanine deoxyribonucleotide, C is cytosine deoxyribonucleotide, T is thymine deoxyribonucleotide, mC is 5-methylcytosine deoxyribonucleotide or mG
Represents O 6 -methylguanine deoxyribonucleotide. The left end is the 5'end and the right end is the 3'end. However, the hydroxyl groups at the 5'end and 3'end of each oligodeoxyribonucleotide are not included. Further, when e, f or g is inserted between A, G, C or T, the phosphodiester group is a phosphorothioate type diester group (e), a methylphosphonate type diester group (f) or methoxyethylaminophosphate. It shows that it has been converted to a type diester group (g).
【００３０】［Ａ群］ＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅ
Ｇ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，Ｔｅ
ＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡ
Ｇ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆ
ＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧ
ＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡ
ｇＧ，ＴＧＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，
ＴＧＧｅＧＧ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧ
ＧＡＧｅＧ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，
ＴＧＣＧＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧ
ｆＧ，ｍＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，Ｇ
ＧＧＣＧＧＧｅＣ，ＴＡＧＧＡＧｅＧ，ＴＧＧＧＡＧＧ
ｅＴ，ＴＧＧＧＣＧＣＡｅＧ，ＣＣｅＧ，ＴＣＧＧＡＧ
ｅＧ，ＴＧｍＣＧＡＧｅＧ，ＧＴＧＧＧＡＧｅＧ，ＴＧ
ｅＧ，ＴＧＧＧＡｍＧｅＧ，ＴＧＧＧＡＧｅＡ，ＡＡＴ
ＧＧＧＡＧｅＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，
ＴＴＧＧｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，
ＴＧＧＧｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧ
ＧｅＧＧ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ，ＣＧＣｅＧ
Ｇ，ＣＧＧＧｅＴ，ＴＧＧＧｅＣ，ＴＧＧＧｅＴ。[Group A] TGGGAeG, TGGGeAe
G, TGGeGeAeG, TGeGeGeAeG, Te
GeGeGeAeG, TGGeGAeG, TGGeGA
G, TGGGAfG, TGGGfAfG, TGGfGf
AfG, TGfGfGfAfG, TGGGAgG, TG
GGgAgG, TGGgGgAgG, TGgGgGgA
gG, TGGGeA, TGGGeG, TGGeGeG,
TGGeGG, TGGeG, TGGGAGeG, CGG
GAGeG, TTGGAGeG, TTGGGAGeG,
TGCGAGeG, GGGGAGeG, mCGGGAG
fG, mCGmCGAGgG, CTGGGAGeG, G
GGCGGGeC, TAGGAGeG, TGGGAGG
eT, TGGGCGCAeG, CCeG, TCGGAG
eG, TGmCGAGeG, GTGGGAGeG, TG
eG, TGGGAmGeG, TGGGAGeA, AAT
GGGAGeG, TTGGGeG, TTGGeGeG,
TTGGeGG, TGGGGeG, TGGGeGeG,
TGGGeGG, CGGGeG, CGGeGeG, CG
GeGG, CGCGeG, CGCeGeG, CGCeG
G, CGGGeT, TGGGeC, TGGGeT.
【００３１】［Ｂ群］ＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅ
Ｇ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，Ｔｅ
ＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡ
Ｇ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆ
ＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧ
ＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡ
ｇＧ，ＴＧＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，
ＴＧＧｅＧＧ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧ
ＧＡＧｅＧ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，
ＴＧＣＧＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧ
ｆＧ，ｍＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，Ｔ
ＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，Ｔ
ＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，Ｃ
ＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧ
ｅＧ，ＣＧＣｅＧｅＧ，ＣＧＣｅＧＧ。[Group B] TGGGAeG, TGGGeAe
G, TGGeGeAeG, TGeGeGeAeG, Te
GeGeGeAeG, TGGeGAeG, TGGeGA
G, TGGGAfG, TGGGfAfG, TGGfGf
AfG, TGfGfGfAfG, TGGGAgG, TG
GGgAgG, TGGgGgAgG, TGgGgGgA
gG, TGGGeA, TGGGeG, TGGeGeG,
TGGeGG, TGGeG, TGGGAGeG, CGG
GAGeG, TTGGAGeG, TTGGGAGeG,
TGCGAGeG, GGGGAGeG, mCGGGAG
fG, mCGmCGAGgG, CTGGGAGeG, T
TGGGeG, TTGGeGeG, TTGGeGG, T
GGGGeG, TGGGeGeG, TGGGeGG, C
GGGeG, CGGeGeG, CGGeGG, CGCG
eG, CGCeGeG, CGCeGG.
【００３２】［Ｃ群］ＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅ
Ｇ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，Ｔｅ
ＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡ
Ｇ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆ
ＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧ
ＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡ
ｇＧ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧＧ，
ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，
ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，
ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣ
ＧｅＧ，ＣＧＣｅＧｅＧ，ＣＧＣｅＧＧ。[Group C] TGGGAeG, TGGGeAe
G, TGGeGeAeG, TGeGeGeAeG, Te
GeGeGeAeG, TGGeGAeG, TGGeGA
G, TGGGAfG, TGGGfAfG, TGGfGf
AfG, TGfGfGfAfG, TGGGAgG, TG
GGgAgG, TGGgGgAgG, TGgGgGgA
gG, TGGGeG, TGGeGeG, TGGeGG,
TTGGGeG, TTGGeGeG, TTGGeGG,
TGGGGeG, TGGGeGeG, TGGGeGG,
CGGGeG, CGGeGeG, CGGeGG, CGC
GeG, CGCeGeG, CGCeGG.
【００３３】［Ｄ群］ＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅ
Ｇ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧＧＡｆ
Ｇ，ＴＧＧＧＡｇＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，
ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ，ＣＧＣ
ｅＧＧ。[Group D] TGGGAeG, TGGGeAe
G, TGGeGAeG, TGGeGAG, TGGGAf
G, TGGGAgG, CGGGeG, CGGeGeG,
CGGeGG, CGCGeG, CGCeGeG, CGC
eGG.
【００３４】［Ｅ群］ＴＧＧＧＡｅＧ，ＣＧＧＧｅＧ，
ＣＧＣＧｅＧ。[Group E] TGGGAeG, CGGGeG,
CGCGeG.
【００３５】前記式（１）において、Ｒ1 、Ｒ2 、Ｒ
3 、Ｙ1 及びＺの組み合わせにより得られる５’末端の
好適な基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）としては、トリフェ
ニルメチルオキシ、３，４−（ジベンジルオキシ）ベン
ジルオキシ、３，５−（ジベンジルオキシ）ベンジルオ
キシ、ｔ−ブチルジフェニルシリルオキシ、フェニルフ
ルオレニルオキシ、フェニルキサンテニルオキシ基があ
げられ、さらに好適には、トリフェニルメチルオキシ、
３，４−（ジベンジルオキシ）ベンジルオキシ、３，５
−（ジベンジルオキシ）ベンジルオキシ基又は３，５−
ビス［３，５−（ジベンジルオキシ）ベンジルオキシ］
ベンジルオキシ基である。In the above formula (1), R 1 , R 2 , R
Suitable groups (R 1 R 2 R 3 Z-Y 1 ) at the 5 ′ end obtained by the combination of 3 , Y 1 and Z include triphenylmethyloxy, 3,4- (dibenzyloxy) benzyloxy, 3,5- (dibenzyloxy) benzyloxy, t-butyldiphenylsilyloxy, phenylfluorenyloxy, and phenylxanthenyloxy groups, and more preferably triphenylmethyloxy,
3,4- (dibenzyloxy) benzyloxy, 3,5
-(Dibenzyloxy) benzyloxy group or 3,5-
Bis [3,5- (dibenzyloxy) benzyloxy]
It is a benzyloxy group.
【００３６】前記式（１）において、Ｒ4 、Ｘ、Ｙ2 、
Ｙ3 、Ｙ4 、ｍ及びｎの組み合わせにより得られる３’
末端の好適な基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ
−Ｙ4 ）n ］m Ｈ）としては、水素、メチルホスホリ
ル、２−クロロフェニルホスホリル、−Ｏ−メチルチオ
ホスホリル、メチルホスホニル、メチルチオホスホニ
ル、フェニルホスホニル、２−ヒドロキシエチルホスホ
リル、−Ｏ−（２−ヒドロキシエチル）チオホスホリ
ル、フェニルホスホリル、４−クロロフェニルホスホリ
ル、２−ニトロフェニルホスホリル、４−ニトロフェニ
ルホスホリル、エチルホスホリル、−Ｏ−エチルチオホ
スホリルがあげられ、さらに好適には、水素、メチルホ
スホリル、２−クロロフェニルホスホリル、−Ｏ−メチ
ルチオホスホリル、メチルホスホニル、メチルチオホス
ホニル、フェニルホスホニル、２−ヒドロキシエチルホ
スホリル、−Ｏ−（２−ヒドロキシエチル）チオホスホ
リル基である。In the above formula (1), R 4 , X, Y 2 ,
3'obtained by combining Y 3 , Y 4 , m and n
A suitable terminal group ([P (O) (Y 2 R 4 ) -Y 3- (X
-Y 4) n] The m H), hydrogen, Mechiruhosuhoriru, 2-chlorophenyl phosphoryl, -O- methyl thio phosphoryl, Mechiruhosuhoniru, methyl thio phosphonyl, phenyl phosphonyl, 2-hydroxyethyl phosphoryl, -O- ( 2-hydroxyethyl) thiophosphoryl, phenylphosphoryl, 4-chlorophenylphosphoryl, 2-nitrophenylphosphoryl, 4-nitrophenylphosphoryl, ethylphosphoryl, -O-ethylthiophosphoryl, and more preferably hydrogen and methylphosphoryl. , 2-chlorophenylphosphoryl, -O-methylthiophosphoryl, methylphosphonyl, methylthiophosphonyl, phenylphosphonyl, 2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl group.
【００３７】本発明の化合物において、好適な化合物と
しては、 １）Ｂの鎖長が４乃至８である化合物、 ２）Ｂの鎖長が５乃至６である化合物、 ３）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせにより
得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、ト
リフェニルメチルオキシ、３，４−（ジベンジルオキ
シ）ベンジルオキシ、３，５−（ジベンジルオキシ）ベ
ンジルオキシ、又は３，５−ビス［３，５−（ジベンジ
ルオキシ）ベンジルオキシ］ベンジルオキシ、ｔ−ブチ
ルジフェニルシリルオキシ、フェニルフルオレニルオキ
シ、フェニルキサンテニルオキシ基であり、Ｒ4 、Ｘ、
Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組み合わせにより得られ
る３’末端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ
−Ｙ4 ）n ］m Ｈ）が、水素、メチルホスホリル、２−
クロロフェニルホスホリル、−Ｏ−メチルチオホスホリ
ル、メチルホスホニル、メチルチオホスホニル、フェニ
ルホスホニル、２−ヒドロキシエチルホスホリル、−Ｏ
−（２−ヒドロキシエチル）チオホスホリル、フェニル
ホスホリル、４−クロロフェニルホスホリル、２−ニト
ロフェニルホスホリル、４−ニトロフェニルホスホリ
ル、エチルホスホリル、−Ｏ−エチルチオホスホリルで
あり、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧ
ｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，ＴｅＧｅＧｅＧ
ｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧ
ＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆＡｆＧ，Ｔ
ＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧＧＧｇＡｇ
Ｇ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧ
ＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧ
Ｇ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧＧＡＧｅ
Ｇ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，ＴＧＣＧ
ＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧｆＧ，ｍ
ＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，ＧＧＧＣＧ
ＧＧｅＣ，ＴＡＧＧＡＧｅＧ，ＴＧＧＧＡＧＧｅＴ，Ｔ
ＧＧＧＣＧＣＡｅＧ，ＣＣｅＧ，ＴＣＧＧＡＧｅＧ，Ｔ
ＧｍＣＧＡＧｅＧ，ＧＴＧＧＧＡＧｅＧ，ＴＧｅＧ，Ｔ
ＧＧＧＡｍＧｅＧ，ＴＧＧＧＡＧｅＡ，ＡＡＴＧＧＧＡ
ＧｅＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧ
ｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧ
ｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧ
Ｇ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ，ＣＧＣｅＧＧ，Ｃ
ＧＧＧｅＴ，ＴＧＧＧｅＣ又はＴＧＧＧｅＴである化合
物、 ４）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせにより
得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、ト
リフェニルメチルオキシ、３，４−（ジベンジルオキ
シ）ベンジルオキシ、３，５−（ジベンジルオキシ）ベ
ンジルオキシ、３，５−ビス［３，５−（ジベンジルオ
キシ）ベンジルオキシ］ベンジルオキシ、ｔ−ブチルジ
フェニルシリルオキシ、フェニルフルオレニルオキシ、
フェニルキサンテニルオキシ基であり、Ｒ4 、Ｘ、Ｙ
2 、Ｙ3 、Ｙ4 、ｍ及びｎの組み合わせにより得られる
３’末端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−
Ｙ4 ）n ］m Ｈ）が、水素、メチルホスホリル、２−ク
ロロフェニルホスホリル、−Ｏ−メチルチオホスホリ
ル、メチルホスホニル、メチルチオホスホニル、フェニ
ルホスホニル、２−ヒドロキシエチルホスホリル、−Ｏ
−（２−ヒドロキシエチル）チオホスホリル、フェニル
ホスホリル、４−クロロフェニルホスホリル、２−ニト
ロフェニルホスホリル、４−ニトロフェニルホスホリ
ル、エチルホスホリル、−Ｏ−エチルチオホスホリルで
あり、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧ
ｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，ＴｅＧｅＧｅＧ
ｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧ
ＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆＡｆＧ，Ｔ
ＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧＧＧｇＡｇ
Ｇ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧ
ＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧ
Ｇ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧＧＡＧｅ
Ｇ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，ＴＧＣＧ
ＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧｆＧ，ｍ
ＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，ＴＴＧＧＧ
ｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，ＴＧＧＧＧ
ｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，ＣＧＧＧｅ
Ｇ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，Ｃ
ＧＣｅＧｅＧ又はＣＧＣｅＧＧである化合物、 ５）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせにより
得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、ト
リフェニルメチルオキシ、３，４−（ジベンジルオキ
シ）ベンジルオキシ、３，５−（ジベンジルオキシ）ベ
ンジルオキシ、３，５−ビス［３，５−（ジベンジルオ
キシ）ベンジルオキシ］ベンジルオキシ、ｔ−ブチルジ
フェニルシリルオキシ、フェニルフルオレニルオキシ、
フェニルキサンテニルオキシ基であり、Ｒ4 、Ｘ、Ｙ
2 、Ｙ3 、Ｙ4 、ｍ及びｎの組み合わせにより得られる
３’末端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−
Ｙ4 ）n ］m Ｈ）が、水素、メチルホスホリル、２−ク
ロロフェニルホスホリル、−Ｏ−メチルチオホスホリ
ル、メチルホスホニル、メチルチオホスホニル、フェニ
ルホスホニル、２−ヒドロキシエチルホスホリル、−Ｏ
−（２−ヒドロキシエチル）チオホスホリル基であり、
ＢがＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧｅＧｅ
ＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，ＴｅＧｅＧｅＧｅＡｅ
Ｇ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧＧＡｆ
Ｇ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆＡｆＧ，ＴＧｆＧ
ｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧＧＧｇＡｇＧ，Ｔ
ＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧＧＧｅ
Ａ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧＧ，Ｔ
ＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧＧＡＧｅＧ，ＴＴ
ＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，ＴＧＣＧＡＧｅ
Ｇ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧｆＧ，ｍＣＧｍ
ＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，ＴＴＧＧＧｅＧ，
ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，ＴＧＧＧＧｅＧ，
ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，ＣＧＧＧｅＧ，Ｃ
ＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，ＣＧＣｅ
ＧｅＧ又はＣＧＣｅＧＧである化合物、 ６）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせにより
得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、ト
リフェニルメチルオキシ、３，４−（ジベンジルオキ
シ）ベンジルオキシ、３，５−（ジベンジルオキシ）ベ
ンジルオキシ基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、
ｍ及びｎの組み合わせにより得られる３’末端の基
（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−Ｙ4 ）n ］m
Ｈ）が、水素、メチルホスホリル、２−クロロフェニル
ホスホリル、−Ｏ−メチルチオホスホリル、メチルホス
ホニル、メチルチオホスホニル、フェニルホスホニル、
２−ヒドロキシエチルホスホリル、−Ｏ−（２−ヒドロ
キシエチル）チオホスホリル、フェニルホスホリル、４
−クロロフェニルホスホリル、２−ニトロフェニルホス
ホリル、４−ニトロフェニルホスホリル、エチルホスホ
リル、−Ｏ−エチルチオホスホリルであり、ＢがＴＧＧ
ＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧｅＧｅＡｅＧ，Ｔ
ＧｅＧｅＧｅＡｅＧ，ＴｅＧｅＧｅＧｅＡｅＧ，ＴＧＧ
ｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧＧＡｆＧ，ＴＧＧ
ＧｆＡｆＧ，ＴＧＧｆＧｆＡｆＧ，ＴＧｆＧｆＧｆＡｆ
Ｇ，ＴＧＧＧＡｇＧ，ＴＧＧＧｇＡｇＧ，ＴＧＧｇＧｇ
ＡｇＧ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧＧＧｅＡ，ＴＧＧ
ＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧＧ，ＴＧＧｅＧ，
ＴＧＧＧＡＧｅＧ，ＣＧＧＧＡＧｅＧ，ＴＴＧＧＡＧｅ
Ｇ，ＴＴＧＧＧＡＧｅＧ，ＴＧＣＧＡＧｅＧ，ＧＧＧＧ
ＡＧｅＧ，ｍＣＧＧＧＡＧｆＧ，ｍＣＧｍＣＧＡＧｇ
Ｇ，ＣＴＧＧＧＡＧｅＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅ
ＧｅＧ，ＴＴＧＧｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅ
ＧｅＧ，ＴＧＧＧｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅ
Ｇ，ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ又は
ＣＧＣｅＧＧである化合物、 ７）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせにより
得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、ト
リフェニルメチルオキシ、３，４−（ジベンジルオキ
シ）ベンジルオキシ、３，５−（ジベンジルオキシ）ベ
ンジルオキシ基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、
ｍ及びｎの組み合わせにより得られる３’末端の基
（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−Ｙ4 ）n ］m
Ｈ）が水素、メチルホスホリル、２−クロロフェニルホ
スホリル、−Ｏ−メチルチオホスホリル、メチルホスホ
ニル、メチルチオホスホニル、フェニルホスホニル、２
−ヒドロキシエチルホスホリル、−Ｏ−（２−ヒドロキ
シエチル）チオホスホリル基であり、ＢがＴＧＧＧＡｅ
Ｇ，ＴＧＧＧｅＡｅＧ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧ
ｅＧｅＡｅＧ，ＴｅＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡ
ｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡ
ｆＧ，ＴＧＧｆＧｆＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，Ｔ
ＧＧＧＡｇＧ，ＴＧＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇ
Ｇ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧＧＧｅＡ，ＴＧＧＧｅ
Ｇ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧＧ，ＴＧＧｅＧ，ＴＧ
ＧＧＡＧｅＧ，ＣＧＧＧＡＧｅＧ，ＴＴＧＧＡＧｅＧ，
ＴＴＧＧＧＡＧｅＧ，ＴＧＣＧＡＧｅＧ，ＧＧＧＧＡＧ
ｅＧ，ｍＣＧＧＧＡＧｆＧ，ｍＣＧｍＣＧＡＧｇＧ，Ｃ
ＴＧＧＧＡＧｅＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅ
Ｇ，ＴＴＧＧｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅ
Ｇ，ＴＧＧＧｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，
ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ，ＣＧＣ
ｅＧＧである化合物 ８）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせにより
得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、ト
リフェニルメチルオキシ基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ
3 、Ｙ4 、ｍ及びｎの組み合わせにより得られる３’末
端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−Ｙ4 ）
n ］m Ｈ）が水素、メチルホスホリル、２−ヒドロキシ
エチルホスホリル、−Ｏ−（２−ヒドロキシエチル）チ
オホスホリル基であり、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧ
ｅＡｅＧ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅ
Ｇ，ＴｅＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧ
ＧｅＧＡＧ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧ
ＧｆＧｆＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇ
Ｇ，ＴＧＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧ
ｇＧｇＡｇＧ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧ
ｅＧＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧ
ｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧ
ｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧ
Ｇ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ又はＣＧＣｅＧＧで
ある化合物、 ９）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせにより
得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、
３，４−（ジベンジルオキシ）ベンジルオキシ、基であ
り、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組み合わ
せにより得られる３’末端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ
4 ）−Ｙ3 −（Ｘ−Ｙ4 ）n ］m Ｈ）が水素、メチルホ
スホリル、２−ヒドロキシエチルホスホリル、−Ｏ−
（２−ヒドロキシエチル）チオホスホリル基であり、Ｂ
がＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧｅＧｅＡ
ｅＧ，ＴＧｅＧｅＧｅＡｅＧ，ＴｅＧｅＧｅＧｅＡｅ
Ｇ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧＧＡｆ
Ｇ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆＡｆＧ，ＴＧｆＧ
ｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧＧＧｇＡｇＧ，Ｔ
ＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧＧＧｅ
Ｇ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧＧ，ＴＴＧＧＧｅＧ，
ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，ＴＧＧＧＧｅＧ，
ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，ＣＧＧＧｅＧ，Ｃ
ＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，ＣＧＣｅ
ＧｅＧ又はＣＧＣｅＧＧである化合物、 １０）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせによ
り得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、
３，４−（ジベンジルオキシ）ベンジルオキシ、基であ
り、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組み合わ
せにより得られる３’末端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ
4 ）−Ｙ3 −（Ｘ−Ｙ4 ）n ］m Ｈ）が水素、メチルホ
スホリル、２−ヒドロキシエチルホスホリル、−Ｏ−
（２−ヒドロキシエチル）チオホスホリル基であり、Ｂ
がＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧｅＧＡｅ
Ｇ，ＴＧＧｅＧＡＧ，ＴＧＧＧＡｆＧ，ＴＧＧＧＡｇ
Ｇ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，Ｃ
ＧＣＧｅＧ，ＣＧＣｅＧｅＧ又はＣＧＣｅＧＧである化
合物、 １１）Ｒ1 、Ｒ2 、Ｒ3 、Ｙ1 及びＺの組み合わせによ
り得られる５’末端の基（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、
３，４−（ジベンジルオキシ）ベンジルオキシ、基であ
り、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組み合わ
せにより得られる３’末端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ
4 ）−Ｙ3 −（Ｘ−Ｙ4 ）n ］m Ｈ）が水素、メチルホ
スホリル、２−ヒドロキシエチルホスホリル、−Ｏ−
（２−ヒドロキシエチル）チオホスホリル基であり、Ｂ
がＴＧＧＧＡｅＧ，ＣＧＧＧｅＧ又はＣＧＣＧｅＧであ
る化合物、をあげることができる。Among the compounds of the present invention, preferred compounds include 1) a compound having a chain length of B of 4 to 8; 2) a compound having a chain length of B of 5 to 6; 3) R 1 and R 2 , R 3 , Y 1 and Z are combined to give a 5′-terminal group (R 1 R 2 R 3 Z-Y 1 ) is triphenylmethyloxy, 3,4- (dibenzyloxy) benzyloxy, 3 , 5- (dibenzyloxy) benzyloxy, or 3,5-bis [3,5- (dibenzyloxy) benzyloxy] benzyloxy, t-butyldiphenylsilyloxy, phenylfluorenyloxy, phenylxanthenyloxy And R 4 , X,
Y 2, Y 3, Y 4 , are obtained by a combination of m and n 3 'end of the group ([P (O) (Y 2 R 4) -Y 3 - (X
-Y 4 ) n ] m H) is hydrogen, methylphosphoryl, 2-
Chlorophenylphosphoryl, -O-methylthiophosphoryl, methylphosphonyl, methylthiophosphonyl, phenylphosphonyl, 2-hydroxyethylphosphoryl, -O
-(2-hydroxyethyl) thiophosphoryl, phenylphosphoryl, 4-chlorophenylphosphoryl, 2-nitrophenylphosphoryl, 4-nitrophenylphosphoryl, ethylphosphoryl, -O-ethylthiophosphoryl, and B is TGGGAeG, TGGGeAeG, TGG.
eGeAeG, TGeGeGeAeG, TeGeGeG
eAeG, TGGeGAeG, TGGeGAG, TGG
GAfG, TGGGfAfG, TGGfGfAfG, T
GfGfGfAfG, TGGGAgG, TGGGgAg
G, TGGgGgAgG, TGgGgGgAgG, TG
GGeA, TGGGeG, TGGeGeG, TGGeG
G, TGGeG, TGGGAGeG, CGGGAGe
G, TTGGAGeG, TTGGGAGeG, TGCG
AGeG, GGGGAGeG, mCGGGAGfG, m
CGmCGAGgG, CTGGGAGeG, GGGCG
GGeC, TAGGAGeG, TGGGAGGeT, T
GGGGCGCAeG, CCeG, TCGGAGeG, T
GmCGAGeG, GTGGGAGeG, TGeG, T
GGGAmGeG, TGGGAGeA, AATGGGA
GeG, TTGGGeG, TTGGeGeG, TTGG
eGG, TGGGGeG, TGGGeGeG, TGGG
eGG, CGGGeG, CGGeGeG, CGGeG
G, CGCGeG, CGCeGeG, CGCeGG, C
A compound which is GGGeT, TGGGeC or TGGGeT, 4) a 5′-terminal group (R 1 R 2 R 3 Z—Y 1 ) obtained by a combination of R 1 , R 2 , R 3 , Y 1 and Z is triphenyl. Methyloxy, 3,4- (dibenzyloxy) benzyloxy, 3,5- (dibenzyloxy) benzyloxy, 3,5-bis [3,5- (dibenzyloxy) benzyloxy] benzyloxy, t- Butyldiphenylsilyloxy, phenylfluorenyloxy,
Phenylxanthenyloxy group, R 4 , X, Y
2, Y 3, Y 4, are obtained by a combination of m and n 3 'end of the group ([P (O) (Y 2 R 4) -Y 3 - (X-
Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-chlorophenyl phosphoryl, -O- methyl thio phosphoryl, Mechiruhosuhoniru, methyl thio phosphonyl, phenyl phosphonyl, 2-hydroxyethyl phosphoryl, -O
-(2-hydroxyethyl) thiophosphoryl, phenylphosphoryl, 4-chlorophenylphosphoryl, 2-nitrophenylphosphoryl, 4-nitrophenylphosphoryl, ethylphosphoryl, -O-ethylthiophosphoryl, and B is TGGGAeG, TGGGeAeG, TGG.
eGeAeG, TGeGeGeAeG, TeGeGeG
eAeG, TGGeGAeG, TGGeGAG, TGG
GAfG, TGGGfAfG, TGGfGfAfG, T
GfGfGfAfG, TGGGAgG, TGGGgAg
G, TGGgGgAgG, TGgGgGgAgG, TG
GGeA, TGGGeG, TGGeGeG, TGGeG
G, TGGeG, TGGGAGeG, CGGGAGe
G, TTGGAGeG, TTGGGAGeG, TGCG
AGeG, GGGGAGeG, mCGGGAGfG, m
CGmCGAGgG, CTGGGAGeG, TTGGG
eG, TTGGeGeG, TTGGeGG, TGGGGG
eG, TGGGeGeG, TGGGeGG, CGGGe
G, CGGeGeG, CGGeGG, CGCGeG, C
A compound which is GCeGeG or CGCeGG, 5) a 5′-terminal group (R 1 R 2 R 3 Z—Y 1 ) obtained by a combination of R 1 , R 2 , R 3 , Y 1 and Z is triphenylmethyloxy 3,4- (dibenzyloxy) benzyloxy, 3,5- (dibenzyloxy) benzyloxy, 3,5-bis [3,5- (dibenzyloxy) benzyloxy] benzyloxy, t-butyldiphenyl Silyloxy, phenylfluorenyloxy,
Phenylxanthenyloxy group, R 4 , X, Y
2, Y 3, Y 4, are obtained by a combination of m and n 3 'end of the group ([P (O) (Y 2 R 4) -Y 3 - (X-
Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-chlorophenyl phosphoryl, -O- methyl thio phosphoryl, Mechiruhosuhoniru, methyl thio phosphonyl, phenyl phosphonyl, 2-hydroxyethyl phosphoryl, -O
A-(2-hydroxyethyl) thiophosphoryl group,
B is TGGGAeG, TGGGeAeG, TGGeGe
AeG, TGeGeGeAeG, TeGeGeGeGeAe
G, TGGeGAeG, TGGeGAG, TGGGAf
G, TGGGfAfG, TGGfGfAfG, TGfG
fGfAfG, TGGGAgG, TGGGgAgG, T
GGgGgAgG, TGgGgGgAgG, TGGGe
A, TGGGeG, TGGeGeG, TGGeGG, T
GGeG, TGGGAGeG, CGGGAGeG, TT
GGAGeG, TTGGGAGeG, TGCGAGe
G, GGGGAGeG, mCGGGAGfG, mCGm
CGAGgG, CTGGGAGeG, TTGGGeG,
TTGGeGeG, TTGGeGG, TGGGGeG,
TGGGeGeG, TGGGeGG, CGGGeG, C
GGeGeG, CGGeGG, CGCGeG, CGCe
A compound which is GeG or CGCeGG, 6) the group at the 5 ′ end (R 1 R 2 R 3 Z—Y 1 ) obtained by the combination of R 1 , R 2 , R 3 , Y 1 and Z is triphenylmethyloxy , 3,4- (dibenzyloxy) benzyloxy, 3,5- (dibenzyloxy) benzyloxy group, and R 4 , X, Y 2 , Y 3 , Y 4 ,
A 3'-terminal group ([P (O) (Y 2 R 4 ) -Y 3- (X-Y 4 ) n ] m obtained by combining m and n.
H) is hydrogen, methylphosphoryl, 2-chlorophenylphosphoryl, -O-methylthiophosphoryl, methylphosphonyl, methylthiophosphonyl, phenylphosphonyl,
2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl, phenylphosphoryl, 4
-Chlorophenylphosphoryl, 2-nitrophenylphosphoryl, 4-nitrophenylphosphoryl, ethylphosphoryl, -O-ethylthiophosphoryl, and B is TGG.
GAeG, TGGGeAeG, TGGeGeAeG, T
GeGeGeAeG, TeGeGeGeGeAeG, TGG
eGAeG, TGGeGAG, TGGGAfG, TGG
GfAfG, TGGfGfAfG, TGfGfGfAf
G, TGGGAgG, TGGGgAgG, TGGgGg
AgG, TGgGgGgAgG, TGGGeA, TGG
GeG, TGGeGeG, TGGeGG, TGGeG,
TGGGAGeG, CGGGAGeG, TTGGAGe
G, TTGGGAGeG, TGCGAGeG, GGGG
AGeG, mCGGGAGfG, mCGmCGAGg
G, CTGGGAGeG, TTGGGeG, TTGGe
GeG, TTGGeGG, TGGGGeG, TGGGe
GeG, TGGGeGG, CGGGeG, CGGeGe
G, CGGeGG, CGCGeG, compounds which are CGCeGeG or CGCeGG, 7) R 1, R 2, R 3, obtained by the combination of Y 1 and Z 5 'end of the group (R 1 R 2 R 3 Z -Y 1) Is a triphenylmethyloxy, 3,4- (dibenzyloxy) benzyloxy, 3,5- (dibenzyloxy) benzyloxy group, and R 4 , X, Y 2 , Y 3 , Y 4 ,
A 3'-terminal group ([P (O) (Y 2 R 4 ) -Y 3- (X-Y 4 ) n ] m obtained by combining m and n.
H) is hydrogen, methylphosphoryl, 2-chlorophenylphosphoryl, -O-methylthiophosphoryl, methylphosphonyl, methylthiophosphonyl, phenylphosphonyl, 2
-Hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl group, B is TGGGAe
G, TGGGeAeG, TGGeGeAeG, TGeG
eGeAeG, TeGeGeGeGeAeG, TGGeGA
eG, TGGGeGAG, TGGGAfG, TGGGfA
fG, TGGfGfAfG, TGfGfGfAfG, T
GGGAgG, TGGGgAgG, TGGgGgAg
G, TGgGgGgAgG, TGGGeA, TGGGe
G, TGGeGeG, TGGeGG, TGGeG, TG
GGAGeG, CGGGAGeG, TTGGAGeG,
TTGGGAGeG, TGCGAGeG, GGGGAG
eG, mCGGGAGfG, mCGmCGAGgG, C
TGGGAGeG, TTGGGeG, TTGGeGe
G, TTGGeGG, TGGGGeG, TGGGeGe
G, TGGGeGG, CGGGeG, CGGeGeG,
CGGeGG, CGCGeG, CGCeGeG, CGC
Compound which is eGG 8) The group at the 5 ′ end obtained by the combination of R 1 , R 2 , R 3 , Y 1 and Z (R 1 R 2 R 3 Z-Y 1 ) is a triphenylmethyloxy group. , R 4 , X, Y 2 , Y
3, Y 4, 3 is obtained by a combination of m and n 'terminus of groups ([P (O) (Y 2 R 4) -Y 3 - (X-Y 4)
n ] m H) is hydrogen, methylphosphoryl, 2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl group, and B is TGGGAeG, TGGG.
eAeG, TGGeGeAeG, TGeGeGeAe
G, TeGeGeGeGeAeG, TGGeGAeG, TG
GeGAG, TGGGAfG, TGGGfAfG, TG
GfGfAfG, TGfGfGfAfG, TGGGAg
G, TGGGgAgG, TGGgGgAgG, TGgG
gGgAgG, TGGGeG, TGGeGeG, TGG
eGG, TTGGGeG, TTGGeGeG, TTGG
eGG, TGGGGeG, TGGGeGeG, TGGG
eGG, CGGGeG, CGGeGeG, CGGeG
G, CGCGeG, CGCeGeG or a compound which is CGCeGG, 9) a 5'terminal group (R 1 R 2 R 3 Z-Y 1 ) obtained by a combination of R 1 , R 2 , R 3 , Y 1 and Z,
3,4 (dibenzyloxy) benzyloxy, a group, R 4, X, Y 2 , Y 3, Y 4, 3 is obtained by a combination of m and n 'terminus of groups ([P (O) ( Y 2 R
4) -Y 3 - (X- Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-hydroxyethyl phosphoryl, -O-
(2-hydroxyethyl) thiophosphoryl group, B
Is TGGGAeG, TGGGeAeG, TGGeGeA
eG, TGeGeGeAeG, TeGeGeGeGeAe
G, TGGeGAeG, TGGeGAG, TGGGAf
G, TGGGfAfG, TGGfGfAfG, TGfG
fGfAfG, TGGGAgG, TGGGgAgG, T
GGgGgAgG, TGgGgGgAgG, TGGGe
G, TGGeGeG, TGGeGG, TTGGGeG,
TTGGeGeG, TTGGeGG, TGGGGeG,
TGGGeGeG, TGGGeGG, CGGGeG, C
GGeGeG, CGGeGG, CGCGeG, CGCe
A compound which is GeG or CGCeGG, 10) a group at the 5 ′ end (R 1 R 2 R 3 Z—Y 1 ) obtained by a combination of R 1 , R 2 , R 3 , Y 1 and Z,
3,4 (dibenzyloxy) benzyloxy, a group, R 4, X, Y 2 , Y 3, Y 4, 3 is obtained by a combination of m and n 'terminus of groups ([P (O) ( Y 2 R
4) -Y 3 - (X- Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-hydroxyethyl phosphoryl, -O-
(2-hydroxyethyl) thiophosphoryl group, B
Is TGGGAeG, TGGGeAeG, TGGeGAe
G, TGGeGAG, TGGGAfG, TGGGAg
G, CGGGeG, CGGeGeG, CGGeGG, C
A compound which is GCGeG, CGCeGeG or CGCeGG, 11) a 5′-terminal group (R 1 R 2 R 3 Z—Y 1 ) obtained by a combination of R 1 , R 2 , R 3 , Y 1 and Z,
3,4 (dibenzyloxy) benzyloxy, a group, R 4, X, Y 2 , Y 3, Y 4, 3 is obtained by a combination of m and n 'terminus of groups ([P (O) ( Y 2 R
4) -Y 3 - (X- Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-hydroxyethyl phosphoryl, -O-
(2-hydroxyethyl) thiophosphoryl group, B
A compound in which is TGGGAeG, CGGGeG or CGCGeG.
【００３８】本発明の代表的化合物としては、例えば、
表１に記載する化合物を挙げることができるが、本発明
はこれらの化合物に限定されるものではない。表中、Me
はメチルを、Etはエチルを、Prはプロピルを、Buはブチ
ルを、 tBuはｔ−ブチルを、3,4-DBP は３、４−（ジベ
ンジルオキシ）フェニルを、3,5-BDBBP は３、５−ビス
｛３、５−（ジベンジルオキシ）ベンジルオキシ｝フェ
ニルを、3,5-DBP は３、５−（ジベンジルオキシ）フェ
ニルを、 1-PYRはピレン−１−イルを、 2-NAPはナフタ
レン−２−イルを、 4-PhPh は４−（フェニル）フェニ
ルを、2-PhPhは２−（フェニル）フェニルを、 9-ANTは
アントラセン−９−イルを、 2-ANTはアントラセン−２
−イルを、 1-NAPはナフタレン−１−イルを、 2-ANQは
アントラキノン−２−イルを、4-PHE はフェナンスレン
−４−イルを、 PhEは１、４−フェニレンを、 2-NH2Et
は２−アミノエチルを、 2-MeOEtは２−メトキシエチル
を、 1-Me-PrE は１−メチルプロピレンを、 2-Me-BuE
は２−メチルブチレンを、2-OH-PrE は２−ヒドロキシ
プロピレンを、「1-1 」はＴＧＧＧＡｅＧを，「1-2 」
はＴＧＧＧｅＡｅＧを，「1-3 」はＴＧＧｅＧｅＡｅＧ
を，「1-4 」はＴＧｅＧｅＧｅＡｅＧを，「1-5 」はＴ
ｅＧｅＧｅＧｅＡｅＧを，「1-6 」はＴＧＧｅＧＡｅＧ
を，「1-7 」はＴＧＧｅＧＡＧを，「1-8 」はＴＧＧＧ
ＡｆＧを，「1-9 」はＴＧＧＧｆＡｆＧを，「1-10」は
ＴＧＧｆＧｆＡｆＧを，「1-11」はＴＧｆＧｆＧｆＡｆ
Ｇを，「1-12」はＴＧＧＧＡｇＧを，「1-13」はＴＧＧ
ＧｇＡｇＧを，「1-14」はＴＧＧｇＧｇＡｇＧを，「1-
15」はＴＧｇＧｇＧｇＡｇＧを，「」はＴＧＧＧｅＡ
を，「3-1 」はＴＧＧＧｅＧを，「3-2 」はＴＧＧｅＧ
ｅＧを，「3-3 」はＴＧＧｅＧＧを，「」はＴＧＧｅ
Ｇを，「」はＴＧＧＧＡＧｅＧを，「」はＣＧＧＧ
ＡＧｅＧを，「」はＴＴＧＧＡＧｅＧを，「」はＴ
ＴＧＧＧＡＧｅＧを，「」はＴＧＣＧＡＧｅＧを，
「イ」はＧＧＧＧＡＧｅＧを，「ロ」はｍＣＧＧＧＡＧ
ｆＧを，「ハ」はｍＣＧｍＣＧＡＧｇＧを，「ニ」はＣ
ＴＧＧＧＡＧｅＧを，「ホ」はＧＧＧＣＧＧＧｅＣを，
「ヘ」はＴＡＧＧＡＧｅＧを，「ト」はＴＧＧＧＡＧＧ
ｅＴを，「チ」はＴＧＧＧＣＧＣＡｅＧを，「リ」はＣ
ＣｅＧを，「ヌ」はＴＣＧＧＡＧｅＧを，「ル」はＴＧ
ｍＣＧＡＧｅＧを，「ヲ」はＧＴＧＧＧＡＧｅＧを，
「ワ」はＴＧｅＧを，「カ」はＴＧＧＧＡｍＧｅＧを，
「ヨ」はＴＧＧＧＡＧｅＡを，「タ」はＡＡＴＧＧＧＡ
ＧｅＧを，「a-1 」はＴＴＧＧＧｅＧを，「a-2 」はＴ
ＴＧＧｅＧｅＧを，「a-3」はＴＴＧＧｅＧＧを，「b-1
」はＴＧＧＧｅＧｅＧを，「b-2 」はＴＧＧＧｅＧＧ
を，「c-1 」はＣＧＧＧｅＧを，「c-2 」はＣＧＧｅＧ
ｅＧを，「c-3 」はＣＧＧｅＧＧを，「d-1 」はＣＧＣ
ＧｅＧを，「d-2 」はＣＧＣｅＧｅＧを，「d-3 」はＣ
ＧＣｅＧＧを，「ｅ」はＣＧＧＧｅＴを，「ｆ」はＴＧ
ＧＧｅＣを，「ｇ」はＴＧＧＧｅＴを示す。Representative compounds of the present invention include, for example:
The compounds listed in Table 1 can be mentioned, but the present invention is not limited to these compounds. In the table, Me
Is methyl, Et is ethyl, Pr is propyl, Bu is butyl, tBu is t-butyl, 3,4-DBP is 3,4- (dibenzyloxy) phenyl, and 3,5-BDBBP is 3,5-bis {3,5- (dibenzyloxy) benzyloxy} phenyl, 3,5-DBP is 3,5- (dibenzyloxy) phenyl, 1-PYR is pyren-1-yl, 2-NAP is naphthalen-2-yl, 4-PhPh is 4- (phenyl) phenyl, 2-PhPh is 2- (phenyl) phenyl, 9-ANT is anthracene-9-yl, and 2-ANT is Anthracene-2
-Yl, 1-NAP is naphthalen-1-yl, 2-ANQ is anthraquinone-2-yl, 4-PHE is phenanthren-4-yl, PhE is 1,4-phenylene, 2-NH 2 Et
Is 2-aminoethyl, 2-MeOEt is 2-methoxyethyl, 1-Me-PrE is 1-methylpropylene, 2-Me-BuE
Is 2-methylbutylene, 2-OH-PrE is 2-hydroxypropylene, "1-1" is TGGGAeG, and "1-2" is
Is TGGGeAeG, "1-3" is TGGeGeAeG
"1-4" is TGeGeGeAeG, and "1-5" is T
eGeGeGeGeAeG, "1-6" is TGGeGAeG
"1-7" is TGGeGAG and "1-8" is TGGG
AfG, “1-9” is TGGGfAfG, “1-10” is TGGfGfAfG, and “1-11” is TGfGfGfAf.
G, "1-12" is TGGGAgG, "1-13" is TGG
GgAgG, "1-14" is TGGgGgAgG, "1-
15 "is TGgGgGgAgG, and""is TGGGeA
"3-1" is TGGGeG, "3-2" is TGGeG
eG, "3-3" is TGGeGG, and "" is TGGe
G, “” is TGGGAGeG, and “” is CGGG
AGeG, "" is TTGGAGeG, "" is T
TGGGAGeG, “” is TGCGAGeG,
“A” means GGGGAGeG, “B” means mCGGGAG
fG, "ha" is mCGmCGAGgG, and "d" is C
TGGGAGeG, "ho" is GGGCGGGeC,
“F” means TAGGAGeG, “TO” means TGGGAGG
eT, "chi" is TGGGCGCAeG, and "ri" is C
CeG, "nu" is TCGGAGeG, and "ru" is TG
mCGAGeG, "wo" is GTGGGAGeG,
"Wa" is TGeG, "Ka" is TGGGAmGeG,
“Yo” is TGGGAGeA, “Ta” is AATGGGA
GeG, "a-1" is TTGGGeG, "a-2" is T
TGGeGeG, "a-3" is TTGGeGG, "b-1
"Is TGGGeGeG, and" b-2 "is TGGGeGG.
"C-1" is CGGGeG, "c-2" is CGGeG
eG, "c-3" is CGG eGG, "d-1" is CGC
GeG, "d-2" is CGCeGeG, and "d-3" is C
GCeGG, "e" is CGGGeT, "f" is TG
GGeC and “g” represent TGGGeT.
【００３９】[0039]
【化６】 [Chemical 6]
【００４０】[0040]
【表１】 ──────────────────────────────────── 番号 R1 R2 R3 Z Y1 Y2 R4 Y3 X Y4 n m 配列 ──────────────────────────────────── 1 3,4-DBP H H C O O H O CH2CH2 O 1 1 1-1 2 3,4-DBP H H C O S H O CH2CH2 O 1 1 1-1 3 3,4-DBP H H C O - - - - - 0 0 1-1 4 3,4-DBP H H C O O Me O - - 0 1 1-1 5 3,4-DBP H H C O O Me S - - 0 1 1-1 6 3,4-DBP H H C O O 2-ClPh O - - 0 1 1-1 7 3,4-DBP H H C O CH2 H O - - 0 1 1-1 8 3,4-DBP H H C O CH2 H S - - 0 1 1-1 9 3,4-DBP H H C O PhE H O - - 0 1 1-1 10 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 1-1 11 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 1-1 12 Ph Ph Ph C O O H O CH2CH2 O 1 1 1-1 13 Ph Ph Ph C O S H O CH2CH2 O 1 1 1-1 14 Ph Ph Ph C O - - - - - 0 0 1-1 15 Ph Ph Ph C O O Me O - - 0 1 1-1 16 Ph Ph Ph C O O Me S - - 0 1 1-1 17 Ph Ph Ph C O O 2-ClPh O - - 0 1 1-1 18 Ph Ph Ph C O CH2 H O - - 0 1 1-1 19 Ph Ph Ph C O CH2 H S - - 0 1 1-1 20 Ph Ph Ph C O PhE H O - - 0 1 1-1 21 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 1-1 22 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 1-1 23 3,5-DBP H H C O O H O CH2CH2 O 1 1 1-1 24 3,5-DBP H H C O S H O CH2CH2 O 1 1 1-1 25 3,5-DBP H H C O - - - - - 0 0 1-1 26 3,5-DBP H H C O O Me O - - 0 1 1-1 27 3,5-DBP H H C O O Me S - - 0 1 1-1 28 3,5-DBP H H C O O 2-ClPh O - - 0 1 1-1 29 3,5-DBP H H C O CH2 H O - - 0 1 1-1 30 3,5-DBP H H C O CH2 H S - - 0 1 1-1 31 3,5-DBP H H C O PhE H O - - 0 1 1-1 32 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 1-1 33 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 1-1 34 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 1-1 35 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 1-1 36 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 1-1 37 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 1-1 38 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 1-1 39 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 1-1 40 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 1-1 41 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 1-1 42 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 1-1 43 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 1-1 44 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 1-1 45 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 46 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 1-1 47 4-MeOPh Ph Ph C O - - - - - 0 0 1-1 48 4-MeOPh Ph Ph C O O Me O - - 0 1 1-1 49 4-MeOPh Ph Ph C O O Me S - - 0 1 1-1 50 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 1-1 51 4-MeOPh Ph Ph C O CH2 H O - - 0 1 1-1 52 4-MeOPh Ph Ph C O CH2 H S - - 0 1 1-1 53 4-MeOPh Ph Ph C O PhE H O - - 0 1 1-1 54 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 1-1 55 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 1-1 56 tBu Ph Ph Si O O H O CH2CH2 O 1 1 1-1 57 tBu Ph Ph Si O S H O CH2CH2 O 1 1 1-1 58 tBu Ph Ph Si O - - - - - 0 0 1-1 59 tBu Ph Ph Si O O Me O - - 0 1 1-1 60 tBu Ph Ph Si O O Me S - - 0 1 1-1 61 tBu Ph Ph Si O O 2-ClPh O - - 0 1 1-1 62 tBu Ph Ph Si O CH2 H O - - 0 1 1-1 63 tBu Ph Ph Si O CH2 H S - - 0 1 1-1 64 tBu Ph Ph Si O PhE H O - - 0 1 1-1 65 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 1-1 66 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 1-1 67 Ph Ph Ph C S O H O CH2CH2 O 1 1 1-1 68 Ph Ph Ph C S S H O CH2CH2 O 1 1 1-1 69 Ph Ph Ph C S - - - - - 0 0 1-1 70 Ph Ph Ph C S O Me O - - 0 1 1-1 71 Ph Ph Ph C S O Me S - - 0 1 1-1 72 Ph Ph Ph C S O 2-ClPh O - - 0 1 1-1 73 Ph Ph Ph C S CH2 H O - - 0 1 1-1 74 Ph Ph Ph C S CH2 H S - - 0 1 1-1 75 Ph Ph Ph C S PhE H O - - 0 1 1-1 76 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 1-1 77 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 1-1 78 4-BnOPh H H C O O H O CH2CH2 O 1 1 1-1 79 4-BnOPh H H C O S H O CH2CH2 O 1 1 1-1 80 4-BnOPh H H C O - - - - - 0 0 1-1 81 4-BnOPh H H C O O Me O - - 0 1 1-1 82 4-BnOPh H H C O O Me S - - 0 1 1-1 83 4-BnOPh H H C O O 2-ClPh O - - 0 1 1-1 84 4-BnOPh H H C O CH2 H O - - 0 1 1-1 85 4-BnOPh H H C O CH2 H S - - 0 1 1-1 86 4-BnOPh H H C O PhE H O - - 0 1 1-1 87 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 1-1 88 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 1-1 89 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 1-1 90 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 1-1 91 Ph Xanthen-9-yl O - - - - - 0 0 1-1 92 Ph Xanthen-9-yl O O Me O - - 0 1 1-1 93 Ph Xanthen-9-yl O O Me S - - 0 1 1-1 94 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 1-1 95 Ph Xanthen-9-yl O CH2 H O - - 0 1 1-1 96 Ph Xanthen-9-yl O CH2 H S - - 0 1 1-1 97 Ph Xanthen-9-yl O PhE H O - - 0 1 1-1 98 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 1-1 99 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 1-1 100 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 1-1 101 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 1-1 102 Ph Fluoren-9-yl O - - - - - 0 0 1-1 103 Ph Fluoren-9-yl O O Me O - - 0 1 1-1 104 Ph Fluoren-9-yl O O Me S - - 0 1 1-1 105 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 1-1 106 Ph Fluoren-9-yl O CH2 H O - - 0 1 1-1 107 Ph Fluoren-9-yl O CH2 H S - - 0 1 1-1 108 Ph Fluoren-9-yl O PhE H O - - 0 1 1-1 109 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 1-1 110 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 1-1 111 3,4-DBP H H C O O H O CH2CH2 O 1 1 112 3,4-DBP H H C O S H O CH2CH2 O 1 1 113 3,4-DBP H H C O - - - - - 0 0 114 3,4-DBP H H C O O Me O - - 0 1 115 3,4-DBP H H C O O Me S - - 0 1 116 3,4-DBP H H C O O 2-ClPh O - - 0 1 117 3,4-DBP H H C O CH2 H O - - 0 1 118 3,4-DBP H H C O CH2 H S - - 0 1 119 3,4-DBP H H C O PhE H O - - 0 1 120 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 121 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 122 Ph Ph Ph C O O H O CH2CH2 O 1 1 123 Ph Ph Ph C O S H O CH2CH2 O 1 1 124 Ph Ph Ph C O - - - - - 0 0 125 Ph Ph Ph C O O Me O - - 0 1 126 Ph Ph Ph C O O Me S - - 0 1 127 Ph Ph Ph C O O 2-ClPh O - - 0 1 128 Ph Ph Ph C O CH2 H O - - 0 1 129 Ph Ph Ph C O CH2 H S - - 0 1 130 Ph Ph Ph C O PhE H O - - 0 1 131 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 132 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 133 3,5-DBP H H C O O H O CH2CH2 O 1 1 134 3,5-DBP H H C O S H O CH2CH2 O 1 1 135 3,5-DBP H H C O - - - - - 0 0 136 3,5-DBP H H C O O Me O - - 0 1 137 3,5-DBP H H C O O Me S - - 0 1 138 3,5-DBP H H C O O 2-ClPh O - - 0 1 139 3,5-DBP H H C O CH2 H O - - 0 1 140 3,5-DBP H H C O CH2 H S - - 0 1 141 3,5-DBP H H C O PhE H O - - 0 1 142 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 143 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 144 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 145 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 146 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 147 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 148 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 149 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 150 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 151 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 152 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 153 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 154 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 155 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 156 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 157 4-MeOPh Ph Ph C O - - - - - 0 0 158 4-MeOPh Ph Ph C O O Me O - - 0 1 159 4-MeOPh Ph Ph C O O Me S - - 0 1 160 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 161 4-MeOPh Ph Ph C O CH2 H O - - 0 1 162 4-MeOPh Ph Ph C O CH2 H S - - 0 1 163 4-MeOPh Ph Ph C O PhE H O - - 0 1 164 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 165 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 166 tBu Ph Ph Si O O H O CH2CH2 O 1 1 167 tBu Ph Ph Si O S H O CH2CH2 O 1 1 168 tBu Ph Ph Si O - - - - - 0 0 169 tBu Ph Ph Si O O Me O - - 0 1 170 tBu Ph Ph Si O O Me S - - 0 1 171 tBu Ph Ph Si O O 2-ClPh O - - 0 1 172 tBu Ph Ph Si O CH2 H O - - 0 1 173 tBu Ph Ph Si O CH2 H S - - 0 1 174 tBu Ph Ph Si O PhE H O - - 0 1 175 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 176 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 177 Ph Ph Ph C S O H O CH2CH2 O 1 1 178 Ph Ph Ph C S S H O CH2CH2 O 1 1 179 Ph Ph Ph C S - - - - - 0 0 180 Ph Ph Ph C S O Me O - - 0 1 181 Ph Ph Ph C S O Me S - - 0 1 182 Ph Ph Ph C S O 2-ClPh O - - 0 1 183 Ph Ph Ph C S CH2 H O - - 0 1 184 Ph Ph Ph C S CH2 H S - - 0 1 185 Ph Ph Ph C S PhE H O - - 0 1 186 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 187 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 188 4-BnOPh H H C O O H O CH2CH2 O 1 1 189 4-BnOPh H H C O S H O CH2CH2 O 1 1 190 4-BnOPh H H C O - - - - - 0 0 191 4-BnOPh H H C O O Me O - - 0 1 192 4-BnOPh H H C O O Me S - - 0 1 193 4-BnOPh H H C O O 2-ClPh O - - 0 1 194 4-BnOPh H H C O CH2 H O - - 0 1 195 4-BnOPh H H C O CH2 H S - - 0 1 196 4-BnOPh H H C O PhE H O - - 0 1 197 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 198 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 199 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 200 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 201 Ph Xanthen-9-yl O - - - - - 0 0 202 Ph Xanthen-9-yl O O Me O - - 0 1 203 Ph Xanthen-9-yl O O Me S - - 0 1 204 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 205 Ph Xanthen-9-yl O CH2 H O - - 0 1 206 Ph Xanthen-9-yl O CH2 H S - - 0 1 207 Ph Xanthen-9-yl O PhE H O - - 0 1 208 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 209 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 210 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 211 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 212 Ph Fluoren-9-yl O - - - - - 0 0 213 Ph Fluoren-9-yl O O Me O - - 0 1 214 Ph Fluoren-9-yl O O Me S - - 0 1 215 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 216 Ph Fluoren-9-yl O CH2 H O - - 0 1 217 Ph Fluoren-9-yl O CH2 H S - - 0 1 218 Ph Fluoren-9-yl O PhE H O - - 0 1 219 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 220 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 221 3,4-DBP H H C O O H O CH2CH2 O 1 1 3-1 222 3,4-DBP H H C O S H O CH2CH2 O 1 1 3-1 223 3,4-DBP H H C O - - - - - 0 0 3-1 224 3,4-DBP H H C O O Me O - - 0 1 3-1 225 3,4-DBP H H C O O Me S - - 0 1 3-1 226 3,4-DBP H H C O O 2-ClPh O - - 0 1 3-1 227 3,4-DBP H H C O CH2 H O - - 0 1 3-1 228 3,4-DBP H H C O CH2 H S - - 0 1 3-1 229 3,4-DBP H H C O PhE H O - - 0 1 3-1 230 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 3-1 231 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 3-1 232 Ph Ph Ph C O O H O CH2CH2 O 1 1 3-1 233 Ph Ph Ph C O S H O CH2CH2 O 1 1 3-1 234 Ph Ph Ph C O - - - - - 0 0 3-1 235 Ph Ph Ph C O O Me O - - 0 1 3-1 236 Ph Ph Ph C O O Me S - - 0 1 3-1 237 Ph Ph Ph C O O 2-ClPh O - - 0 1 3-1 238 Ph Ph Ph C O CH2 H O - - 0 1 3-1 239 Ph Ph Ph C O CH2 H S - - 0 1 3-1 240 Ph Ph Ph C O PhE H O - - 0 1 3-1 241 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 3-1 242 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 3-1 243 3,5-DBP H H C O O H O CH2CH2 O 1 1 3-1 244 3,5-DBP H H C O S H O CH2CH2 O 1 1 3-1 245 3,5-DBP H H C O - - - - - 0 0 3-1 246 3,5-DBP H H C O O Me O - - 0 1 3-1 247 3,5-DBP H H C O O Me S - - 0 1 3-1 248 3,5-DBP H H C O O 2-ClPh O - - 0 1 3-1 249 3,5-DBP H H C O CH2 H O - - 0 1 3-1 250 3,5-DBP H H C O CH2 H S - - 0 1 3-1 251 3,5-DBP H H C O PhE H O - - 0 1 3-1 252 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 3-1 253 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 3-1 254 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 3-1 255 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 3-1 256 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 3-1 257 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 3-1 258 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 3-1 259 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 3-1 260 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 3-1 261 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 3-1 262 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 3-1 263 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 3-1 264 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 3-1 265 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 3-1 266 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 3-1 267 4-MeOPh Ph Ph C O - - - - - 0 0 3-1 268 4-MeOPh Ph Ph C O O Me O - - 0 1 3-1 269 4-MeOPh Ph Ph C O O Me S - - 0 1 3-1 270 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 3-1 271 4-MeOPh Ph Ph C O CH2 H O - - 0 1 3-1 272 4-MeOPh Ph Ph C O CH2 H S - - 0 1 3-1 273 4-MeOPh Ph Ph C O PhE H O - - 0 1 3-1 274 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 3-1 275 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 3-1 276 tBu Ph Ph Si O O H O CH2CH2 O 1 1 3-1 277 tBu Ph Ph Si O S H O CH2CH2 O 1 1 3-1 278 tBu Ph Ph Si O - - - - - 0 0 3-1 279 tBu Ph Ph Si O O Me O - 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- 0 1 3-1 306 4-BnOPh H H C O PhE H O - - 0 1 3-1 307 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 3-1 308 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 3-1 309 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 3-1 310 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 3-1 311 Ph Xanthen-9-yl O - - - - - 0 0 3-1 312 Ph Xanthen-9-yl O O Me O - - 0 1 3-1 313 Ph Xanthen-9-yl O O Me S - - 0 1 3-1 314 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 3-1 315 Ph Xanthen-9-yl O CH2 H O - - 0 1 3-1 316 Ph Xanthen-9-yl O CH2 H S - - 0 1 3-1 317 Ph Xanthen-9-yl O PhE H O - - 0 1 3-1 318 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 3-1 319 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 3-1 320 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 3-1 321 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 3-1 322 Ph Fluoren-9-yl O - - - - - 0 0 3-1 323 Ph Fluoren-9-yl O O Me O - - 0 1 3-1 324 Ph Fluoren-9-yl O O Me S - - 0 1 3-1 325 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 3-1 326 Ph Fluoren-9-yl O CH2 H O - - 0 1 3-1 327 Ph Fluoren-9-yl O CH2 H S - - 0 1 3-1 328 Ph Fluoren-9-yl O PhE H O - - 0 1 3-1 329 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 3-1 330 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 3-1 331 3,4-DBP H H C O O H O CH2CH2 O 1 1 332 3,4-DBP H H C O S H O CH2CH2 O 1 1 333 3,4-DBP H H C O - - - - - 0 0 334 3,4-DBP H H C O O Me O - - 0 1 335 3,4-DBP H H C O O Me S - - 0 1 336 3,4-DBP H H C O O 2-ClPh O - - 0 1 337 3,4-DBP H H C O CH2 H O - - 0 1 338 3,4-DBP H H C O CH2 H S - - 0 1 339 3,4-DBP H H C O PhE H O - - 0 1 340 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 341 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 342 Ph Ph Ph C O O H O CH2CH2 O 1 1 343 Ph Ph Ph C O S H O CH2CH2 O 1 1 344 Ph Ph Ph C O - - - - - 0 0 345 Ph Ph Ph C O O Me O - - 0 1 346 Ph Ph Ph C O O Me S - - 0 1 347 Ph Ph Ph C O O 2-ClPh O - - 0 1 348 Ph Ph Ph C O CH2 H O - - 0 1 349 Ph Ph Ph C O CH2 H S - - 0 1 350 Ph Ph Ph C O PhE H O - - 0 1 351 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 352 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 353 3,5-DBP H H C O O H O CH2CH2 O 1 1 354 3,5-DBP H H C O S H O CH2CH2 O 1 1 355 3,5-DBP H H C O - - - - - 0 0 356 3,5-DBP H H C O O Me O - - 0 1 357 3,5-DBP H H C O O Me S - - 0 1 358 3,5-DBP H H C O O 2-ClPh O - 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- - - - 0 0 466 3,5-DBP H H C O O Me O - - 0 1 467 3,5-DBP H H C O O Me S - - 0 1 468 3,5-DBP H H C O O 2-ClPh O - - 0 1 469 3,5-DBP H H C O CH2 H O - - 0 1 470 3,5-DBP H H C O CH2 H S - - 0 1 471 3,5-DBP H H C O PhE H O - - 0 1 472 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 473 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 474 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 475 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 476 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 477 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 478 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 479 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 480 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 481 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 482 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 483 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 484 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 485 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 486 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 487 4-MeOPh Ph Ph C O - - - - - 0 0 488 4-MeOPh Ph Ph C O O Me O - - 0 1 489 4-MeOPh Ph Ph C O O Me S - - 0 1 490 4-MeOPh Ph Ph C O O 2-ClPh O - 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- - - - 0 0 961 4-BnOPh H H C O O Me O - - 0 1 962 4-BnOPh H H C O O Me S - - 0 1 963 4-BnOPh H H C O O 2-ClPh O - - 0 1 964 4-BnOPh H H C O CH2 H O - - 0 1 965 4-BnOPh H H C O CH2 H S - - 0 1 966 4-BnOPh H H C O PhE H O - - 0 1 967 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 968 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 969 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 970 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 971 Ph Xanthen-9-yl O - - - - - 0 0 972 Ph Xanthen-9-yl O O Me O - - 0 1 973 Ph Xanthen-9-yl O O Me S - - 0 1 974 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 975 Ph Xanthen-9-yl O CH2 H O - - 0 1 976 Ph Xanthen-9-yl O CH2 H S - - 0 1 977 Ph Xanthen-9-yl O PhE H O - - 0 1 978 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 979 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 980 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 981 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 982 Ph Fluoren-9-yl O - - - - - 0 0 983 Ph Fluoren-9-yl O O Me O - - 0 1 984 Ph Fluoren-9-yl O O Me S - - 0 1 985 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 986 Ph Fluoren-9-yl O CH2 H O - 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1 1 イ 1013 3,5-DBP H H C O O H O CH2CH2 O 1 1 イ 1014 3,5-DBP H H C O S H O CH2CH2 O 1 1 イ 1015 3,5-DBP H H C O - - - - - 0 0 イ 1016 3,5-DBP H H C O O Me O - - 0 1 イ 1017 3,5-DBP H H C O O Me S - - 0 1 イ 1018 3,5-DBP H H C O O 2-ClPh O - - 0 1 イ 1019 3,5-DBP H H C O CH2 H O - - 0 1 イ 1020 3,5-DBP H H C O CH2 H S - - 0 1 イ 1021 3,5-DBP H H C O PhE H O - - 0 1 イ 1022 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 イ 1023 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 イ 1024 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 イ 1025 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 イ 1026 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 イ 1027 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 イ 1028 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 イ 1029 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 イ 1030 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 イ 1031 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 イ 1032 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 イ 1033 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 イ 1034 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 イ 1035 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 イ 1036 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 イ 1037 4-MeOPh Ph Ph C O - - - - - 0 0 イ 1038 4-MeOPh Ph Ph C O O Me O - - 0 1 イ 1039 4-MeOPh Ph Ph C O O Me S - - 0 1 イ 1040 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 イ 1041 4-MeOPh Ph Ph C O CH2 H O - - 0 1 イ 1042 4-MeOPh Ph Ph C O CH2 H S - - 0 1 イ 1043 4-MeOPh Ph Ph C O PhE H O - - 0 1 イ 1044 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 イ 1045 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 イ 1046 tBu Ph Ph Si O O H O CH2CH2 O 1 1 イ 1047 tBu Ph Ph Si O S H O CH2CH2 O 1 1 イ 1048 tBu Ph Ph Si O - - - - - 0 0 イ 1049 tBu Ph Ph Si O O Me O - - 0 1 イ 1050 tBu Ph Ph Si O O Me S - - 0 1 イ 1051 tBu Ph Ph Si O O 2-ClPh O - - 0 1 イ 1052 tBu Ph Ph Si O CH2 H O - - 0 1 イ 1053 tBu Ph Ph Si O CH2 H S - - 0 1 イ 1054 tBu Ph Ph Si O PhE H O - - 0 1 イ 1055 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 イ 1056 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 イ 1057 Ph Ph Ph C S O H O CH2CH2 O 1 1 イ 1058 Ph Ph Ph C S S H O CH2CH2 O 1 1 イ 1059 Ph Ph Ph C S - - - - - 0 0 イ 1060 Ph Ph Ph C S O Me O - - 0 1 イ 1061 Ph Ph Ph C S O Me S - - 0 1 イ 1062 Ph Ph Ph C S O 2-ClPh O - - 0 1 イ 1063 Ph Ph Ph C S CH2 H O - - 0 1 イ 1064 Ph Ph Ph C S CH2 H S - - 0 1 イ 1065 Ph Ph Ph C S PhE H O - - 0 1 イ 1066 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 イ 1067 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 イ 1068 4-BnOPh H H C O O H O CH2CH2 O 1 1 イ 1069 4-BnOPh H H C O S H O CH2CH2 O 1 1 イ 1070 4-BnOPh H H C O - - - - - 0 0 イ 1071 4-BnOPh H H C O O Me O - - 0 1 イ 1072 4-BnOPh H H C O O Me S - - 0 1 イ 1073 4-BnOPh H H C O O 2-ClPh O - - 0 1 イ 1074 4-BnOPh H H C O CH2 H O - - 0 1 イ 1075 4-BnOPh H H C O CH2 H S - - 0 1 イ 1076 4-BnOPh H H C O PhE H O - - 0 1 イ 1077 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 イ 1078 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 イ 1079 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 イ 1080 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 イ 1081 Ph Xanthen-9-yl O - - - - - 0 0 イ 1082 Ph Xanthen-9-yl O O Me O - - 0 1 イ 1083 Ph Xanthen-9-yl O O Me S - - 0 1 イ 1084 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 イ 1085 Ph Xanthen-9-yl O CH2 H O - - 0 1 イ 1086 Ph Xanthen-9-yl O CH2 H S - - 0 1 イ 1087 Ph Xanthen-9-yl O PhE H O - - 0 1 イ 1088 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 イ 1089 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 イ 1090 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 イ 1091 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 イ 1092 Ph Fluoren-9-yl O - - - - - 0 0 イ 1093 Ph Fluoren-9-yl O O Me O - - 0 1 イ 1094 Ph Fluoren-9-yl O O Me S - - 0 1 イ 1095 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 イ 1096 Ph Fluoren-9-yl O CH2 H O - - 0 1 イ 1097 Ph Fluoren-9-yl O CH2 H S - - 0 1 イ 1098 Ph Fluoren-9-yl O PhE H O - - 0 1 イ 1099 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 イ 1100 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 イ 1101 3,4-DBP H H C O O H O CH2CH2 O 1 1 ロ 1102 3,4-DBP H H C O S H O CH2CH2 O 1 1 ロ 1103 3,4-DBP H H C O - - - - - 0 0 ロ 1104 3,4-DBP H H C O O Me O - - 0 1 ロ 1105 3,4-DBP H H C O O Me S - - 0 1 ロ 1106 3,4-DBP H H C O O 2-ClPh O - - 0 1 ロ 1107 3,4-DBP H H C O CH2 H O - - 0 1 ロ 1108 3,4-DBP H H C O CH2 H S - - 0 1 ロ 1109 3,4-DBP H H C O PhE H O - - 0 1 ロ 1110 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ロ 1111 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ロ 1112 Ph Ph Ph C O O H O CH2CH2 O 1 1 ロ 1113 Ph Ph Ph C O S H O CH2CH2 O 1 1 ロ 1114 Ph Ph Ph C O - - - - - 0 0 ロ 1115 Ph Ph Ph C O O Me O - - 0 1 ロ 1116 Ph Ph Ph C O O Me S - - 0 1 ロ 1117 Ph Ph Ph C O O 2-ClPh O - - 0 1 ロ 1118 Ph Ph Ph C O CH2 H O - - 0 1 ロ 1119 Ph Ph Ph C O CH2 H S - - 0 1 ロ 1120 Ph Ph Ph C O PhE H O - - 0 1 ロ 1121 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 ロ 1122 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 ロ 1123 3,5-DBP H H C O O H O CH2CH2 O 1 1 ロ 1124 3,5-DBP H H C O S H O CH2CH2 O 1 1 ロ 1125 3,5-DBP H H C O - - - - - 0 0 ロ 1126 3,5-DBP H H C O O Me O - - 0 1 ロ 1127 3,5-DBP H H C O O Me S - - 0 1 ロ 1128 3,5-DBP H H C O O 2-ClPh O - - 0 1 ロ 1129 3,5-DBP H H C O CH2 H O - - 0 1 ロ 1130 3,5-DBP H H C O CH2 H S - - 0 1 ロ 1131 3,5-DBP H H C O PhE H O - - 0 1 ロ 1132 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 ロ 1133 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 ロ 1134 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 ロ 1135 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 ロ 1136 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 ロ 1137 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 ロ 1138 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 ロ 1139 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 ロ 1140 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 ロ 1141 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 ロ 1142 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 ロ 1143 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 ロ 1144 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 ロ 1145 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 ロ 1146 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 ロ 1147 4-MeOPh Ph Ph C O - - - - - 0 0 ロ 1148 4-MeOPh Ph Ph C O O Me O - - 0 1 ロ 1149 4-MeOPh Ph Ph C O O Me S - - 0 1 ロ 1150 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 ロ 1151 4-MeOPh Ph Ph C O CH2 H O - - 0 1 ロ 1152 4-MeOPh Ph Ph C O CH2 H S - - 0 1 ロ 1153 4-MeOPh Ph Ph C O PhE H O - - 0 1 ロ 1154 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 ロ 1155 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 ロ 1156 tBu Ph Ph Si O O H O CH2CH2 O 1 1 ロ 1157 tBu Ph Ph Si O S H O CH2CH2 O 1 1 ロ 1158 tBu Ph Ph Si O - - - - - 0 0 ロ 1159 tBu Ph Ph Si O O Me O - - 0 1 ロ 1160 tBu Ph Ph Si O O Me S - - 0 1 ロ 1161 tBu Ph Ph Si O O 2-ClPh O - - 0 1 ロ 1162 tBu Ph Ph Si O CH2 H O - - 0 1 ロ 1163 tBu Ph Ph Si O CH2 H S - - 0 1 ロ 1164 tBu Ph Ph Si O PhE H O - - 0 1 ロ 1165 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 ロ 1166 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 ロ 1167 Ph Ph Ph C S O H O CH2CH2 O 1 1 ロ 1168 Ph Ph Ph C S S H O CH2CH2 O 1 1 ロ 1169 Ph Ph Ph C S - - - - - 0 0 ロ 1170 Ph Ph Ph C S O Me O - - 0 1 ロ 1171 Ph Ph Ph C S O Me S - - 0 1 ロ 1172 Ph Ph Ph C S O 2-ClPh O - - 0 1 ロ 1173 Ph Ph Ph C S CH2 H O - - 0 1 ロ 1174 Ph Ph Ph C S CH2 H S - - 0 1 ロ 1175 Ph Ph Ph C S PhE H O - - 0 1 ロ 1176 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 ロ 1177 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 ロ 1178 4-BnOPh H H C O O H O CH2CH2 O 1 1 ロ 1179 4-BnOPh H H C O S H O CH2CH2 O 1 1 ロ 1180 4-BnOPh H H C O - - - - - 0 0 ロ 1181 4-BnOPh H H C O O Me O - - 0 1 ロ 1182 4-BnOPh H H C O O Me S - - 0 1 ロ 1183 4-BnOPh H H C O O 2-ClPh O - - 0 1 ロ 1184 4-BnOPh H H C O CH2 H O - - 0 1 ロ 1185 4-BnOPh H H C O CH2 H S - - 0 1 ロ 1186 4-BnOPh H H C O PhE H O - - 0 1 ロ 1187 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 ロ 1188 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 ロ 1189 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 ロ 1190 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 ロ 1191 Ph Xanthen-9-yl O - - - - - 0 0 ロ 1192 Ph Xanthen-9-yl O O Me O - - 0 1 ロ 1193 Ph Xanthen-9-yl O O Me S - - 0 1 ロ 1194 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 ロ 1195 Ph Xanthen-9-yl O CH2 H O - - 0 1 ロ 1196 Ph Xanthen-9-yl O CH2 H S - - 0 1 ロ 1197 Ph Xanthen-9-yl O PhE H O - - 0 1 ロ 1198 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 ロ 1199 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 ロ 1200 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 ロ 1201 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 ロ 1202 Ph Fluoren-9-yl O - - - - - 0 0 ロ 1203 Ph Fluoren-9-yl O O Me O - - 0 1 ロ 1204 Ph Fluoren-9-yl O O Me S - - 0 1 ロ 1205 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 ロ 1206 Ph Fluoren-9-yl O CH2 H O - - 0 1 ロ 1207 Ph Fluoren-9-yl O CH2 H S - - 0 1 ロ 1208 Ph Fluoren-9-yl O PhE H O - - 0 1 ロ 1209 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 ロ 1210 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 ロ 1211 3,4-DBP H H C O O H O CH2CH2 O 1 1 ハ 1212 3,4-DBP H H C O S H O CH2CH2 O 1 1 ハ 1213 3,4-DBP H H C O - - - - - 0 0 ハ 1214 3,4-DBP H H C O O Me O - - 0 1 ハ 1215 3,4-DBP H H C O O Me S - - 0 1 ハ 1216 3,4-DBP H H C O O 2-ClPh O - - 0 1 ハ 1217 3,4-DBP H H C O CH2 H O - - 0 1 ハ 1218 3,4-DBP H H C O CH2 H S - - 0 1 ハ 1219 3,4-DBP H H C O PhE H O - - 0 1 ハ 1220 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ハ 1221 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ハ 1222 Ph Ph Ph C O O H O CH2CH2 O 1 1 ハ 1223 Ph Ph Ph C O S H O CH2CH2 O 1 1 ハ 1224 Ph Ph Ph C O - - - - - 0 0 ハ 1225 Ph Ph Ph C O O Me O - - 0 1 ハ 1226 Ph Ph Ph C O O Me S - - 0 1 ハ 1227 Ph Ph Ph C O O 2-ClPh O - - 0 1 ハ 1228 Ph Ph Ph C O CH2 H O - - 0 1 ハ 1229 Ph Ph Ph C O CH2 H S - - 0 1 ハ 1230 Ph Ph Ph C O PhE H O - - 0 1 ハ 1231 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 ハ 1232 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 ハ 1233 3,5-DBP H H C O O H O CH2CH2 O 1 1 ハ 1234 3,5-DBP H H C O S H O CH2CH2 O 1 1 ハ 1235 3,5-DBP H H C O - - - - - 0 0 ハ 1236 3,5-DBP H H C O O Me O - - 0 1 ハ 1237 3,5-DBP H H C O O Me S - - 0 1 ハ 1238 3,5-DBP H H C O O 2-ClPh O - - 0 1 ハ 1239 3,5-DBP H H C O CH2 H O - - 0 1 ハ 1240 3,5-DBP H H C O CH2 H S - - 0 1 ハ 1241 3,5-DBP H H C O PhE H O - - 0 1 ハ 1242 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 ハ 1243 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 ハ 1244 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 ハ 1245 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 ハ 1246 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 ハ 1247 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 ハ 1248 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 ハ 1249 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 ハ 1250 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 ハ 1251 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 ハ 1252 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 ハ 1253 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 ハ 1254 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 ハ 1255 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 ハ 1256 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 ハ 1257 4-MeOPh Ph Ph C O - - - - - 0 0 ハ 1258 4-MeOPh Ph Ph C O O Me O - - 0 1 ハ 1259 4-MeOPh Ph Ph C O O Me S - - 0 1 ハ 1260 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 ハ 1261 4-MeOPh Ph Ph C O CH2 H O - - 0 1 ハ 1262 4-MeOPh Ph Ph C O CH2 H S - - 0 1 ハ 1263 4-MeOPh Ph Ph C O PhE H O - - 0 1 ハ 1264 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 ハ 1265 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 ハ 1266 tBu Ph Ph Si O O H O CH2CH2 O 1 1 ハ 1267 tBu Ph Ph Si O S H O CH2CH2 O 1 1 ハ 1268 tBu Ph Ph Si O - - - - - 0 0 ハ 1269 tBu Ph Ph Si O O Me O - - 0 1 ハ 1270 tBu Ph Ph Si O O Me S - - 0 1 ハ 1271 tBu Ph Ph Si O O 2-ClPh O - - 0 1 ハ 1272 tBu Ph Ph Si O CH2 H O - - 0 1 ハ 1273 tBu Ph Ph Si O CH2 H S - - 0 1 ハ 1274 tBu Ph Ph Si O PhE H O - - 0 1 ハ 1275 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 ハ 1276 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 ハ 1277 Ph Ph Ph C S O H O CH2CH2 O 1 1 ハ 1278 Ph Ph Ph C S S H O CH2CH2 O 1 1 ハ 1279 Ph Ph Ph C S - - - - - 0 0 ハ 1280 Ph Ph Ph C S O Me O - - 0 1 ハ 1281 Ph Ph Ph C S O Me S - - 0 1 ハ 1282 Ph Ph Ph C S O 2-ClPh O - - 0 1 ハ 1283 Ph Ph Ph C S CH2 H O - - 0 1 ハ 1284 Ph Ph Ph C S CH2 H S - - 0 1 ハ 1285 Ph Ph Ph C S PhE H O - - 0 1 ハ 1286 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 ハ 1287 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 ハ 1288 4-BnOPh H H C O O H O CH2CH2 O 1 1 ハ 1289 4-BnOPh H H C O S H O CH2CH2 O 1 1 ハ 1290 4-BnOPh H H C O - - - - - 0 0 ハ 1291 4-BnOPh H H C O O Me O - - 0 1 ハ 1292 4-BnOPh H H C O O Me S - - 0 1 ハ 1293 4-BnOPh H H C O O 2-ClPh O - - 0 1 ハ 1294 4-BnOPh H H C O CH2 H O - - 0 1 ハ 1295 4-BnOPh H H C O CH2 H S - - 0 1 ハ 1296 4-BnOPh H H C O PhE H O - - 0 1 ハ 1297 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 ハ 1298 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 ハ 1299 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 ハ 1300 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 ハ 1301 Ph Xanthen-9-yl O - - - - - 0 0 ハ 1302 Ph Xanthen-9-yl O O Me O - - 0 1 ハ 1303 Ph Xanthen-9-yl O O Me S - - 0 1 ハ 1304 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 ハ 1305 Ph Xanthen-9-yl O CH2 H O - - 0 1 ハ 1306 Ph Xanthen-9-yl O CH2 H S - - 0 1 ハ 1307 Ph Xanthen-9-yl O PhE H O - - 0 1 ハ 1308 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 ハ 1309 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 ハ 1310 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 ハ 1311 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 ハ 1312 Ph Fluoren-9-yl O - - - - - 0 0 ハ 1313 Ph Fluoren-9-yl O O Me O - - 0 1 ハ 1314 Ph Fluoren-9-yl O O Me S - - 0 1 ハ 1315 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 ハ 1316 Ph Fluoren-9-yl O CH2 H O - - 0 1 ハ 1317 Ph Fluoren-9-yl O CH2 H S - - 0 1 ハ 1318 Ph Fluoren-9-yl O PhE H O - - 0 1 ハ 1319 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 ハ 1320 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 ハ 1321 3,4-DBP H H C O O H O CH2CH2 O 1 1 ニ 1322 3,4-DBP H H C O S H O CH2CH2 O 1 1 ニ 1323 3,4-DBP H H C O - - - - - 0 0 ニ 1324 3,4-DBP H H C O O Me O - - 0 1 ニ 1325 3,4-DBP H H C O O Me S - - 0 1 ニ 1326 3,4-DBP H H C O O 2-ClPh O - - 0 1 ニ 1327 3,4-DBP H H C O CH2 H O - - 0 1 ニ 1328 3,4-DBP H H C O CH2 H S - - 0 1 ニ 1329 3,4-DBP H H C O PhE H O - - 0 1 ニ 1330 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ニ 1331 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ニ 1332 Ph Ph Ph C O O H O CH2CH2 O 1 1 ニ 1333 Ph Ph Ph C O S H O CH2CH2 O 1 1 ニ 1334 Ph Ph Ph C O - - - - - 0 0 ニ 1335 Ph Ph Ph C O O Me O - - 0 1 ニ 1336 Ph Ph Ph C O O Me S - - 0 1 ニ 1337 Ph Ph Ph C O O 2-ClPh O - - 0 1 ニ 1338 Ph Ph Ph C O CH2 H O - - 0 1 ニ 1339 Ph Ph Ph C O CH2 H S - - 0 1 ニ 1340 Ph Ph Ph C O PhE H O - - 0 1 ニ 1341 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 ニ 1342 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 ニ 1343 3,5-DBP H H C O O H O CH2CH2 O 1 1 ニ 1344 3,5-DBP H H C O S H O CH2CH2 O 1 1 ニ 1345 3,5-DBP H H C O - - - - - 0 0 ニ 1346 3,5-DBP H H C O O Me O - - 0 1 ニ 1347 3,5-DBP H H C O O Me S - - 0 1 ニ 1349 3,5-DBP H H C O CH2 H O - - 0 1 ニ 1350 3,5-DBP H H C O CH2 H S - - 0 1 ニ 1351 3,5-DBP H H C O PhE H O - - 0 1 ニ 1352 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 ニ 1353 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 ニ 1354 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 ニ 1355 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 ニ 1356 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 ニ 1357 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 ニ 1358 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 ニ 1359 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 ニ 1360 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 ニ 1361 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 ニ 1362 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 ニ 1363 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 ニ 1364 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 ニ 1365 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 ニ 1366 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 ニ 1367 4-MeOPh Ph Ph C O - - - - - 0 0 ニ 1368 4-MeOPh Ph Ph C O O Me O - - 0 1 ニ 1369 4-MeOPh Ph Ph C O O Me S - - 0 1 ニ 1370 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 ニ 1371 4-MeOPh Ph Ph C O CH2 H O - - 0 1 ニ 1372 4-MeOPh Ph Ph C O CH2 H S - - 0 1 ニ 1373 4-MeOPh Ph Ph C O PhE H O - - 0 1 ニ 1374 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 ニ 1375 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 ニ 1376 tBu Ph Ph Si O O H O CH2CH2 O 1 1 ニ 1377 tBu Ph Ph Si O S H O CH2CH2 O 1 1 ニ 1378 tBu Ph Ph Si O - - - - - 0 0 ニ 1379 tBu Ph Ph Si O O Me O - - 0 1 ニ 1380 tBu Ph Ph Si O O Me S - - 0 1 ニ 1381 tBu Ph Ph Si O O 2-ClPh O - - 0 1 ニ 1382 tBu Ph Ph Si O CH2 H O - - 0 1 ニ 1383 tBu Ph Ph Si O CH2 H S - - 0 1 ニ 1384 tBu Ph Ph Si O PhE H O - - 0 1 ニ 1385 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 ニ 1386 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 ニ 1387 Ph Ph Ph C S O H O CH2CH2 O 1 1 ニ 1388 Ph Ph Ph C S S H O CH2CH2 O 1 1 ニ 1389 Ph Ph Ph C S - - - - - 0 0 ニ 1390 Ph Ph Ph C S O Me O - - 0 1 ニ 1391 Ph Ph Ph C S O Me S - - 0 1 ニ 1392 Ph Ph Ph C S O 2-ClPh O - - 0 1 ニ 1393 Ph Ph Ph C S CH2 H O - - 0 1 ニ 1394 Ph Ph Ph C S CH2 H S - - 0 1 ニ 1395 Ph Ph Ph C S PhE H O - - 0 1 ニ 1396 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 ニ 1397 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 ニ 1398 4-BnOPh H H C O O H O CH2CH2 O 1 1 ニ 1399 4-BnOPh H H C O S H O CH2CH2 O 1 1 ニ 1400 4-BnOPh H H C O - - - - - 0 0 ニ 1401 4-BnOPh H H C O O Me O - - 0 1 ニ 1402 4-BnOPh H H C O O Me S - - 0 1 ニ 1403 4-BnOPh H H C O O 2-ClPh O - - 0 1 ニ 1404 4-BnOPh H H C O CH2 H O - - 0 1 ニ 1405 4-BnOPh H H C O CH2 H S - - 0 1 ニ 1406 4-BnOPh H H C O PhE H O - - 0 1 ニ 1407 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 ニ 1408 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 ニ 1409 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 ニ 1410 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 ニ 1411 Ph Xanthen-9-yl O - - - - - 0 0 ニ 1412 Ph Xanthen-9-yl O O Me O - - 0 1 ニ 1413 Ph Xanthen-9-yl O O Me S - - 0 1 ニ 1414 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 ニ 1415 Ph Xanthen-9-yl O CH2 H O - - 0 1 ニ 1416 Ph Xanthen-9-yl O CH2 H S - - 0 1 ニ 1417 Ph Xanthen-9-yl O PhE H O - - 0 1 ニ 1418 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 ニ 1419 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 ニ 1420 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 ニ 1421 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 ニ 1422 Ph Fluoren-9-yl O - - - - - 0 0 ニ 1423 Ph Fluoren-9-yl O O Me O - - 0 1 ニ 1424 Ph Fluoren-9-yl O O Me S - - 0 1 ニ 1425 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 ニ 1426 Ph Fluoren-9-yl O CH2 H O - - 0 1 ニ 1427 Ph Fluoren-9-yl O CH2 H S - - 0 1 ニ 1428 Ph Fluoren-9-yl O PhE H O - - 0 1 ニ 1429 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 ニ 1430 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 ニ 1431 3,4-DBP H H C O O H O CH2CH2 O 1 1 ホ 1432 3,4-DBP H H C O S H O CH2CH2 O 1 1 ホ 1433 3,4-DBP H H C O - - - - - 0 0 ホ 1434 3,4-DBP H H C O O Me O - - 0 1 ホ 1435 3,4-DBP H H C O O Me S - - 0 1 ホ 1436 3,4-DBP H H C O O 2-ClPh O - - 0 1 ホ 1437 3,4-DBP H H C O CH2 H O - - 0 1 ホ 1438 3,4-DBP H H C O CH2 H S - - 0 1 ホ 1439 3,4-DBP H H C O PhE H O - - 0 1 ホ 1440 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ホ 1441 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ホ 1442 Ph Ph Ph C O O H O CH2CH2 O 1 1 ホ 1443 Ph Ph Ph C O S H O CH2CH2 O 1 1 ホ 1444 Ph Ph Ph C O - - - - - 0 0 ホ 1445 Ph Ph Ph C O O Me O - - 0 1 ホ 1446 Ph Ph Ph C O O Me S - - 0 1 ホ 1447 Ph Ph Ph C O O 2-ClPh O - - 0 1 ホ 1448 Ph Ph Ph C O CH2 H O - - 0 1 ホ 1449 Ph Ph Ph C O CH2 H S - - 0 1 ホ 1450 Ph Ph Ph C O PhE H O - - 0 1 ホ 1451 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 ホ 1452 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 ホ 1453 3,5-DBP H H C O O H O CH2CH2 O 1 1 ホ 1454 3,5-DBP H H C O S H O CH2CH2 O 1 1 ホ 1455 3,5-DBP H H C O - - - - - 0 0 ホ 1456 3,5-DBP H H C O O Me O - - 0 1 ホ 1457 3,5-DBP H H C O O Me S - - 0 1 ホ 1458 3,5-DBP H H C O O 2-ClPh O - - 0 1 ホ 1459 3,5-DBP H H C O CH2 H O - - 0 1 ホ 1460 3,5-DBP H H C O CH2 H S - - 0 1 ホ 1461 3,5-DBP H H C O PhE H O - - 0 1 ホ 1462 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 ホ 1463 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 ホ 1464 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 ホ 1465 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 ホ 1466 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 ホ 1467 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 ホ 1468 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 ホ 1469 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 ホ 1470 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 ホ 1471 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 ホ 1472 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 ホ 1473 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 ホ 1474 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 ホ 1475 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 ホ 1476 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 ホ 1477 4-MeOPh Ph Ph C O - - - - - 0 0 ホ 1478 4-MeOPh Ph Ph C O O Me O - - 0 1 ホ 1479 4-MeOPh Ph Ph C O O Me S - - 0 1 ホ 1480 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 ホ 1481 4-MeOPh Ph Ph C O CH2 H O - - 0 1 ホ 1482 4-MeOPh Ph Ph C O CH2 H S - - 0 1 ホ 1483 4-MeOPh Ph Ph C O PhE H O - - 0 1 ホ 1484 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 ホ 1485 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 ホ 1486 tBu Ph Ph Si O O H O CH2CH2 O 1 1 ホ 1487 tBu Ph Ph Si O S H O CH2CH2 O 1 1 ホ 1488 tBu Ph Ph Si O - - - - - 0 0 ホ 1489 tBu Ph Ph Si O O Me O - - 0 1 ホ 1490 tBu Ph Ph Si O O Me S - - 0 1 ホ 1491 tBu Ph Ph Si O O 2-ClPh O - - 0 1 ホ 1492 tBu Ph Ph Si O CH2 H O - - 0 1 ホ 1493 tBu Ph Ph Si O CH2 H S - - 0 1 ホ 1494 tBu Ph Ph Si O PhE H O - - 0 1 ホ 1495 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 ホ 1496 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 ホ 1497 Ph Ph Ph C S O H O CH2CH2 O 1 1 ホ 1498 Ph Ph Ph C S S H O CH2CH2 O 1 1 ホ 1499 Ph Ph Ph C S - - - - - 0 0 ホ 1500 Ph Ph Ph C S O Me O - - 0 1 ホ 1501 Ph Ph Ph C S O Me S - - 0 1 ホ 1502 Ph Ph Ph C S O 2-ClPh O - - 0 1 ホ 1503 Ph Ph Ph C S CH2 H O - - 0 1 ホ 1504 Ph Ph Ph C S CH2 H S - - 0 1 ホ 1505 Ph Ph Ph C S PhE H O - - 0 1 ホ 1506 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 ホ 1507 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 ホ 1508 4-BnOPh H H C O O H O CH2CH2 O 1 1 ホ 1509 4-BnOPh H H C O S H O CH2CH2 O 1 1 ホ 1510 4-BnOPh H H C O - - - - - 0 0 ホ 1511 4-BnOPh H H C O O Me O - - 0 1 ホ 1512 4-BnOPh H H C O O Me S - - 0 1 ホ 1513 4-BnOPh H H C O O 2-ClPh O - - 0 1 ホ 1514 4-BnOPh H H C O CH2 H O - - 0 1 ホ 1515 4-BnOPh H H C O CH2 H S - - 0 1 ホ 1516 4-BnOPh H H C O PhE H O - - 0 1 ホ 1517 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 ホ 1518 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 ホ 1519 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 ホ 1520 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 ホ 1521 Ph Xanthen-9-yl O - - - - - 0 0 ホ 1522 Ph Xanthen-9-yl O O Me O - - 0 1 ホ 1523 Ph Xanthen-9-yl O O Me S - - 0 1 ホ 1524 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 ホ 1525 Ph Xanthen-9-yl O CH2 H O - - 0 1 ホ 1526 Ph Xanthen-9-yl O CH2 H S - - 0 1 ホ 1527 Ph Xanthen-9-yl O PhE H O - - 0 1 ホ 1528 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 ホ 1529 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 ホ 1530 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 ホ 1531 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 ホ 1532 Ph Fluoren-9-yl O - - - - - 0 0 ホ 1533 Ph Fluoren-9-yl O O Me O - - 0 1 ホ 1534 Ph Fluoren-9-yl O O Me S - - 0 1 ホ 1535 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 ホ 1536 Ph Fluoren-9-yl O CH2 H O - - 0 1 ホ 1537 Ph Fluoren-9-yl O CH2 H S - - 0 1 ホ 1538 Ph Fluoren-9-yl O PhE H O - - 0 1 ホ 1539 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 ホ 1540 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 ホ 1541 3,4-DBP H H C O O H O CH2CH2 O 1 1 ヘ 1542 3,4-DBP H H C O S H O CH2CH2 O 1 1 ヘ 1543 3,4-DBP H H C O - - - - - 0 0 ヘ 1544 3,4-DBP H H C O O Me O - - 0 1 ヘ 1545 3,4-DBP H H C O O Me S - - 0 1 ヘ 1546 3,4-DBP H H C O O 2-ClPh O - - 0 1 ヘ 1547 3,4-DBP H H C O CH2 H O - - 0 1 ヘ 1548 3,4-DBP H H C O CH2 H S - - 0 1 ヘ 1549 3,4-DBP H H C O PhE H O - - 0 1 ヘ 1550 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ヘ 1551 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ヘ 1552 Ph Ph Ph C O O H O CH2CH2 O 1 1 ヘ 1553 Ph Ph Ph C O S H O CH2CH2 O 1 1 ヘ 1554 Ph Ph Ph C O - - - - - 0 0 ヘ 1555 Ph Ph Ph C O O Me O - - 0 1 ヘ 1556 Ph Ph Ph C O O Me S - - 0 1 ヘ 1557 Ph Ph Ph C O O 2-ClPh O - - 0 1 ヘ 1558 Ph Ph Ph C O CH2 H O - - 0 1 ヘ 1559 Ph Ph Ph C O CH2 H S - - 0 1 ヘ 1560 Ph Ph Ph C O PhE H O - - 0 1 ヘ 1561 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 ヘ 1562 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 ヘ 1563 3,5-DBP H H C O O H O CH2CH2 O 1 1 ヘ 1564 3,5-DBP H H C O S H O CH2CH2 O 1 1 ヘ 1565 3,5-DBP H H C O - - - - - 0 0 ヘ 1566 3,5-DBP H H C O O Me O - - 0 1 ヘ 1567 3,5-DBP H H C O O Me S - - 0 1 ヘ 1568 3,5-DBP H H C O O 2-ClPh O - - 0 1 ヘ 1569 3,5-DBP H H C O CH2 H O - - 0 1 ヘ 1570 3,5-DBP H H C O CH2 H S - - 0 1 ヘ 1571 3,5-DBP H H C O PhE H O - - 0 1 ヘ 1572 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 ヘ 1573 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 ヘ 1574 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 ヘ 1575 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 ヘ 1576 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 ヘ 1577 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 ヘ 1578 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 ヘ 1579 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 ヘ 1580 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 ヘ 1581 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 ヘ 1582 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 ヘ 1583 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 ヘ 1584 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 ヘ 1585 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 ヘ 1586 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 ヘ 1587 4-MeOPh Ph Ph C O - - - - - 0 0 ヘ 1588 4-MeOPh Ph Ph C O O Me O - - 0 1 ヘ 1589 4-MeOPh Ph Ph C O O Me S - - 0 1 ヘ 1590 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 ヘ 1591 4-MeOPh Ph Ph C O CH2 H O - - 0 1 ヘ 1592 4-MeOPh Ph Ph C O CH2 H S - - 0 1 ヘ 1593 4-MeOPh Ph Ph C O PhE H O - - 0 1 ヘ 1594 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 ヘ 1595 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 ヘ 1596 tBu Ph Ph Si O O H O CH2CH2 O 1 1 ヘ 1597 tBu Ph Ph Si O S H O CH2CH2 O 1 1 ヘ 1598 tBu Ph Ph Si O - - - - - 0 0 ヘ 1599 tBu Ph Ph Si O O Me O - - 0 1 ヘ 1600 tBu Ph Ph Si O O Me S - - 0 1 ヘ 1601 tBu Ph Ph Si O O 2-ClPh O - - 0 1 ヘ 1602 tBu Ph Ph Si O CH2 H O - - 0 1 ヘ 1603 tBu Ph Ph Si O CH2 H S - - 0 1 ヘ 1604 tBu Ph Ph Si O PhE H O - - 0 1 ヘ 1605 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 ヘ 1606 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 ヘ 1607 Ph Ph Ph C S O H O CH2CH2 O 1 1 ヘ 1608 Ph Ph Ph C S S H O CH2CH2 O 1 1 ヘ 1609 Ph Ph Ph C S - - - - - 0 0 ヘ 1610 Ph Ph Ph C S O Me O - - 0 1 ヘ 1611 Ph Ph Ph C S O Me S - - 0 1 ヘ 1612 Ph Ph Ph C S O 2-ClPh O - - 0 1 ヘ 1613 Ph Ph Ph C S CH2 H O - - 0 1 ヘ 1614 Ph Ph Ph C S CH2 H S - - 0 1 ヘ 1615 Ph Ph Ph C S PhE H O - - 0 1 ヘ 1616 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 ヘ 1617 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 ヘ 1618 4-BnOPh H H C O O H O CH2CH2 O 1 1 ヘ 1619 4-BnOPh H H C O S H O CH2CH2 O 1 1 ヘ 1620 4-BnOPh H H C O - - - - - 0 0 ヘ 1621 4-BnOPh H H C O O Me O - - 0 1 ヘ 1622 4-BnOPh H H C O O Me S - - 0 1 ヘ 1623 4-BnOPh H H C O O 2-ClPh O - - 0 1 ヘ 1624 4-BnOPh H H C O CH2 H O - - 0 1 ヘ 1625 4-BnOPh H H C O CH2 H S - - 0 1 ヘ 1626 4-BnOPh H H C O PhE H O - - 0 1 ヘ 1627 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 ヘ 1628 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 ヘ 1629 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 ヘ 1630 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 ヘ 1631 Ph Xanthen-9-yl O - - - - - 0 0 ヘ 1632 Ph Xanthen-9-yl O O Me O - - 0 1 ヘ 1633 Ph Xanthen-9-yl O O Me S - - 0 1 ヘ 1634 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 ヘ 1635 Ph Xanthen-9-yl O CH2 H O - - 0 1 ヘ 1636 Ph Xanthen-9-yl O CH2 H S - - 0 1 ヘ 1637 Ph Xanthen-9-yl O PhE H O - - 0 1 ヘ 1638 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 ヘ 1639 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 ヘ 1640 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 ヘ 1641 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 ヘ 1642 Ph Fluoren-9-yl O - - - - - 0 0 ヘ 1643 Ph Fluoren-9-yl O O Me O - - 0 1 ヘ 1644 Ph Fluoren-9-yl O O Me S - - 0 1 ヘ 1645 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 ヘ 1646 Ph Fluoren-9-yl O CH2 H O - - 0 1 ヘ 1647 Ph Fluoren-9-yl O CH2 H S - - 0 1 ヘ 1648 Ph Fluoren-9-yl O PhE H O - - 0 1 ヘ 1649 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 ヘ 1650 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 ヘ 1651 3,4-DBP H H C O O H O CH2CH2 O 1 1 ト 1652 3,4-DBP H H C O S H O CH2CH2 O 1 1 ト 1653 3,4-DBP H H C O - - - - - 0 0 ト 1654 3,4-DBP H H C O O Me O - - 0 1 ト 1655 3,4-DBP H H C O O Me S - - 0 1 ト 1656 3,4-DBP H H C O O 2-ClPh O - - 0 1 ト 1657 3,4-DBP H H C O CH2 H O - - 0 1 ト 1658 3,4-DBP H H C O CH2 H S - - 0 1 ト 1659 3,4-DBP H H C O PhE H O - - 0 1 ト 1660 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ト 1661 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ト 1662 Ph Ph Ph C O O H O CH2CH2 O 1 1 ト 1663 Ph Ph Ph C O S H O CH2CH2 O 1 1 ト 1664 Ph Ph Ph C O - - - - - 0 0 ト 1665 Ph Ph Ph C O O Me O - - 0 1 ト 1666 Ph Ph Ph C O O Me S - - 0 1 ト 1668 Ph Ph Ph C O CH2 H O - - 0 1 ト 1669 Ph Ph Ph C O CH2 H S - - 0 1 ト 1670 Ph Ph Ph C O PhE H O - - 0 1 ト 1671 Ph Ph Ph C O NH Pr O CH2CH2 O 1 1 ト 1672 Ph Ph Ph C O O Me NH (CH2)3 - 1 1 ト 1673 3,5-DBP H H C O O H O CH2CH2 O 1 1 ト 1674 3,5-DBP H H C O S H O CH2CH2 O 1 1 ト 1675 3,5-DBP H H C O - - - - - 0 0 ト 1676 3,5-DBP H H C O O Me O - - 0 1 ト 1677 3,5-DBP H H C O O Me S - - 0 1 ト 1678 3,5-DBP H H C O O 2-ClPh O - - 0 1 ト 1679 3,5-DBP H H C O CH2 H O - - 0 1 ト 1680 3,5-DBP H H C O CH2 H S - - 0 1 ト 1681 3,5-DBP H H C O PhE H O - - 0 1 ト 1682 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 ト 1683 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 ト 1684 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 ト 1685 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 ト 1686 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 ト 1687 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 ト 1688 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 ト 1689 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 ト 1690 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 ト 1691 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 ト 1692 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 ト 1693 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 ト 1694 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 ト 1695 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 ト 1696 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 ト 1697 4-MeOPh Ph Ph C O - - - - - 0 0 ト 1698 4-MeOPh Ph Ph C O O Me O - - 0 1 ト 1699 4-MeOPh Ph Ph C O O Me S - - 0 1 ト 1700 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 ト 1701 4-MeOPh Ph Ph C O CH2 H O - - 0 1 ト 1702 4-MeOPh Ph Ph C O CH2 H S - - 0 1 ト 1703 4-MeOPh Ph Ph C O PhE H O - - 0 1 ト 1704 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 ト 1705 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 ト 1706 tBu Ph Ph Si O O H O CH2CH2 O 1 1 ト 1707 tBu Ph Ph Si O S H O CH2CH2 O 1 1 ト 1708 tBu Ph Ph Si O - - - - - 0 0 ト 1709 tBu Ph Ph Si O O Me O - - 0 1 ト 1710 tBu Ph Ph Si O O Me S - - 0 1 ト 1711 tBu Ph Ph Si O O 2-ClPh O - - 0 1 ト 1712 tBu Ph Ph Si O CH2 H O - - 0 1 ト 1713 tBu Ph Ph Si O CH2 H S - - 0 1 ト 1714 tBu Ph Ph Si O PhE H O - - 0 1 ト 1715 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 ト 1716 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 ト 1717 Ph Ph Ph C S O H O CH2CH2 O 1 1 ト 1718 Ph Ph Ph C S S H O CH2CH2 O 1 1 ト 1719 Ph Ph Ph C S - - - - - 0 0 ト 1720 Ph Ph Ph C S O Me O - - 0 1 ト 1721 Ph Ph Ph C S O Me S - - 0 1 ト 1722 Ph Ph Ph C S O 2-ClPh O - - 0 1 ト 1723 Ph Ph Ph C S CH2 H O - - 0 1 ト 1724 Ph Ph Ph C S CH2 H S - - 0 1 ト 1725 Ph Ph Ph C S PhE H O - - 0 1 ト 1726 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 ト 1727 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 ト 1728 4-BnOPh H H C O O H O CH2CH2 O 1 1 ト 1729 4-BnOPh H H C O S H O CH2CH2 O 1 1 ト 1730 4-BnOPh H H C O - - - - - 0 0 ト 1731 4-BnOPh H H C O O Me O - - 0 1 ト 1732 4-BnOPh H H C O O Me S - - 0 1 ト 1733 4-BnOPh H H C O O 2-ClPh O - - 0 1 ト 1734 4-BnOPh H H C O CH2 H O - - 0 1 ト 1735 4-BnOPh H H C O CH2 H S - - 0 1 ト 1736 4-BnOPh H H C O PhE H O - - 0 1 ト 1737 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 ト 1738 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 ト 1739 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 ト 1740 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 ト 1741 Ph Xanthen-9-yl O - - - - - 0 0 ト 1742 Ph Xanthen-9-yl O O Me O - - 0 1 ト 1743 Ph Xanthen-9-yl O O Me S - - 0 1 ト 1744 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 ト 1745 Ph Xanthen-9-yl O CH2 H O - - 0 1 ト 1746 Ph Xanthen-9-yl O CH2 H S - - 0 1 ト 1747 Ph Xanthen-9-yl O PhE H O - - 0 1 ト 1748 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 ト 1749 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 ト 1750 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 ト 1751 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 ト 1752 Ph Fluoren-9-yl O - - - - - 0 0 ト 1753 Ph Fluoren-9-yl O O Me O - - 0 1 ト 1754 Ph Fluoren-9-yl O O Me S - - 0 1 ト 1755 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 ト 1756 Ph Fluoren-9-yl O CH2 H O - - 0 1 ト 1757 Ph Fluoren-9-yl O CH2 H S - - 0 1 ト 1758 Ph Fluoren-9-yl O PhE H O - - 0 1 ト 1759 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 ト 1760 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 ト 1761 1-PYR H H C O O H O CH2CH2 O 1 1 1-1 1762 1-PYR H H C O S H O CH2CH2 O 1 1 1-1 1763 1-PYR H H C O - - - - - 0 0 1-1 1764 1-PYR H H C O O Me O - - 0 1 1-1 1765 1-PYR H H C O O Me S - - 0 1 1-1 1766 2-NAP H H C O O H O CH2CH2 O 1 1 1-1 1767 2-NAP H H C O S H O CH2CH2 O 1 1 1-1 1768 2-NAP H H C O - - - - - 0 0 1-1 1769 2-NAP H H C O O Me O - - 0 1 1-1 1770 2-NAP H H C O O Me S - - 0 1 1-1 1771 Ph Ph H C O O H O CH2CH2 O 1 1 1-1 1772 Ph Ph H C O S H O CH2CH2 O 1 1 1-1 1773 Ph Ph H C O - - - - - 0 0 1-1 1774 Ph Ph H C O O Me O - - 0 1 1-1 1775 Ph Ph H C O O Me S - - 0 1 1-1 1776 4-PhPh H H C O O H O CH2CH2 O 1 1 1-1 1777 4-PhPh H H C O S H O CH2CH2 O 1 1 1-1 1778 4-PhPh H H C O - - - - - 0 0 1-1 1779 4-PhPh H H C O O Me O - - 0 1 1-1 1780 4-PhPh H H C O O Me S - - 0 1 1-1 1781 2-PhPh H H C O O H O CH2CH2 O 1 1 1-1 1782 2-PhPh H H C O S H O CH2CH2 O 1 1 1-1 1783 2-PhPh H H C O - - - - - 0 0 1-1 1784 2-PhPh H H C O O Me O - - 0 1 1-1 1785 2-PhPh H H C O O Me S - - 0 1 1-1 1786 Ph Ph H C S O H O CH2CH2 O 1 1 1-1 1787 Ph Ph H C S S H O CH2CH2 O 1 1 1-1 1788 Ph Ph H C S - - - - - 0 0 1-1 1789 Ph Ph H C S O Me O - - 0 1 1-1 1790 Ph Ph H C S O Me S - - 0 1 1-1 1791 Ph Ph Ph C NH O H O CH2CH2 O 1 1 1-1 1792 Ph Ph Ph C NH S H O CH2CH2 O 1 1 1-1 1793 Ph Ph Ph C NH - - - - - 0 0 1-1 1794 Ph Ph Ph C NH O Me O - - 0 1 1-1 1795 Ph Ph Ph C NH O Me S - - 0 1 1-1 1796 1-PYR H H C O O H O CH2CH2 O 1 1 1797 1-PYR H H C O S H O CH2CH2 O 1 1 1798 1-PYR H H C O - - - - - 0 0 1799 1-PYR H H C O O Me O - - 0 1 1800 1-PYR H H C O O Me S - - 0 1 1801 2-NAP H H C O O H O CH2CH2 O 1 1 1802 2-NAP H H C O S H O CH2CH2 O 1 1 1803 2-NAP H H C O - - - - - 0 0 1804 2-NAP H H C O O Me O - - 0 1 1805 2-NAP H H C O O Me S - - 0 1 1806 Ph Ph H C O O H O CH2CH2 O 1 1 1807 Ph Ph H C O S H O CH2CH2 O 1 1 1808 Ph Ph H C O - - - - - 0 0 1809 Ph Ph H C O O Me O - - 0 1 1810 Ph Ph H C O O Me S - - 0 1 1811 4-PhPh H H C O O H O CH2CH2 O 1 1 1812 4-PhPh H H C O S H O CH2CH2 O 1 1 1813 4-PhPh H H C O - - - - - 0 0 1814 4-PhPh H H C O O Me O - - 0 1 1815 4-PhPh H H C O O Me S - - 0 1 1816 2-PhPh H H C O O H O CH2CH2 O 1 1 1817 2-PhPh H H C O S H O CH2CH2 O 1 1 1818 2-PhPh H H C O - - - - - 0 0 1819 2-PhPh H H C O O Me O - - 0 1 1820 2-PhPh H H C O O Me S - - 0 1 1821 Ph Ph H C S O H O CH2CH2 O 1 1 1822 Ph Ph H C S S H O CH2CH2 O 1 1 1823 Ph Ph H C S - - - - - 0 0 1824 Ph Ph H C S O Me O - - 0 1 1825 Ph Ph H C S O Me S - - 0 1 1826 Ph Ph Ph C NH O H O CH2CH2 O 1 1 1827 Ph Ph Ph C NH S H O CH2CH2 O 1 1 1828 Ph Ph Ph C NH - - - - - 0 0 1829 Ph Ph Ph C NH O Me O - - 0 1 1830 Ph Ph Ph C NH O Me S - - 0 1 1831 1-PYR H H C O O H O CH2CH2 O 1 1 3-1 1832 1-PYR H H C O S H O CH2CH2 O 1 1 3-1 1833 1-PYR H H C O - - - - - 0 0 3-1 1834 1-PYR H H C O O Me O - - 0 1 3-1 1835 1-PYR H H C O O Me S - - 0 1 3-1 1836 2-NAP H H C O O H O CH2CH2 O 1 1 3-1 1837 2-NAP H H C O S H O CH2CH2 O 1 1 3-1 1838 2-NAP H H C O - - - - - 0 0 3-1 1839 2-NAP H H C O O Me O - - 0 1 3-1 1840 2-NAP H H C O O Me S - - 0 1 3-1 1841 Ph Ph H C O O H O CH2CH2 O 1 1 3-1 1842 Ph Ph H C O S H O CH2CH2 O 1 1 3-1 1843 Ph Ph H C O - - - - - 0 0 3-1 1844 Ph Ph H C O O Me O - - 0 1 3-1 1845 Ph Ph H C O O Me S - - 0 1 3-1 1846 4-PhPh H H C O O H O CH2CH2 O 1 1 3-1 1847 4-PhPh H H C O S H O CH2CH2 O 1 1 3-1 1848 4-PhPh H H C O - - - - - 0 0 3-1 1849 4-PhPh H H C O O Me O - - 0 1 3-1 1850 4-PhPh H H C O O Me S - - 0 1 3-1 1851 2-PhPh H H C O O H O CH2CH2 O 1 1 3-1 1852 2-PhPh H H C O S H O CH2CH2 O 1 1 3-1 1853 2-PhPh H H C O - - - - - 0 0 3-1 1854 2-PhPh H H C O O Me O - - 0 1 3-1 1855 2-PhPh H H C O O Me S - - 0 1 3-1 1856 Ph Ph H C S O H O CH2CH2 O 1 1 3-1 1857 Ph Ph H C S S H O CH2CH2 O 1 1 3-1 1858 Ph Ph H C S - - - - - 0 0 3-1 1859 Ph Ph H C S O Me O - - 0 1 3-1 1860 Ph Ph H C S O Me S - - 0 1 3-1 1861 Ph Ph Ph C NH O H O CH2CH2 O 1 1 3-1 1862 Ph Ph Ph C NH S H O CH2CH2 O 1 1 3-1 1863 Ph Ph Ph C NH - - - - - 0 0 3-1 1864 Ph Ph Ph C NH O Me O - - 0 1 3-1 1865 Ph Ph Ph C NH O Me S - - 0 1 3-1 1866 1-PYR H H C O O H O CH2CH2 O 1 1 1867 1-PYR H H C O S H O CH2CH2 O 1 1 1868 1-PYR H H C O - - - - - 0 0 1869 1-PYR H H C O O Me O - - 0 1 1870 1-PYR H H C O O Me S - - 0 1 1871 2-NAP H H C O O H O CH2CH2 O 1 1 1872 2-NAP H H C O S H O CH2CH2 O 1 1 1873 2-NAP H H C O - - - - - 0 0 1874 2-NAP H H C O O Me O - - 0 1 1875 2-NAP H H C O O Me S - - 0 1 1876 Ph Ph H C O O H O CH2CH2 O 1 1 1877 Ph Ph H C O S H O CH2CH2 O 1 1 1878 Ph Ph H C O - - - - - 0 0 1879 Ph Ph H C O O Me O - - 0 1 1880 Ph Ph H C O O Me S - - 0 1 1881 4-PhPh H H C O O H O CH2CH2 O 1 1 1882 4-PhPh H H C O S H O CH2CH2 O 1 1 1883 4-PhPh H H C O - - - - - 0 0 1884 4-PhPh H H C O O Me O - - 0 1 1885 4-PhPh H H C O O Me S - - 0 1 1886 2-PhPh H H C O O H O CH2CH2 O 1 1 1887 2-PhPh H H C O S H O CH2CH2 O 1 1 1888 2-PhPh H H C O - - - - - 0 0 1889 2-PhPh H H C O O Me O - - 0 1 1890 2-PhPh H H C O O Me S - - 0 1 1891 Ph Ph H C S O H O CH2CH2 O 1 1 1892 Ph Ph H C S S H O CH2CH2 O 1 1 1893 Ph Ph H C S - - - - - 0 0 1894 Ph Ph H C S O Me O - - 0 1 1895 Ph Ph H C S O Me S - - 0 1 1896 Ph Ph Ph C NH O H O CH2CH2 O 1 1 1897 Ph Ph Ph C NH S H O CH2CH2 O 1 1 1898 Ph Ph Ph C NH - - - - - 0 0 1899 Ph Ph Ph C NH O Me O - - 0 1 1900 Ph Ph Ph C NH O Me S - - 0 1 1901 3,4-DBP H H C O O H O CH2CH2 O 1 1 チ 1902 3,4-DBP H H C O S H O CH2CH2 O 1 1 チ 1903 3,4-DBP H H C O - - - - - 0 0 チ 1904 3,4-DBP H H C O O Me O - - 0 1 チ 1905 3,4-DBP H H C O O Me S - - 0 1 チ 1906 Ph Ph Ph C O O H O CH2CH2 O 1 1 チ 1907 Ph Ph Ph C O S H O CH2CH2 O 1 1 チ 1908 Ph Ph Ph C O - - - - - 0 0 チ 1909 Ph Ph Ph C O O Me O - - 0 1 チ 1910 Ph Ph Ph C O O Me S - - 0 1 チ 1911 3,5-DBP H H C O O H O CH2CH2 O 1 1 チ 1912 3,5-DBP H H C O S H O CH2CH2 O 1 1 チ 1913 3,5-DBP H H C O - - - - - 0 0 チ 1914 3,5-DBP H H C O O Me O - - 0 1 チ 1915 3,5-DBP H H C O O Me S - - 0 1 チ 1916 3,4-DBP H H C O O H O CH2CH2 O 1 1 リ 1917 3,4-DBP H H C O S H O CH2CH2 O 1 1 リ 1918 3,4-DBP H H C O - - - - - 0 0 リ 1919 3,4-DBP H H C O O Me O - - 0 1 リ 1920 3,4-DBP H H C O O Me S - - 0 1 リ 1921 Ph Ph Ph C O O H O CH2CH2 O 1 1 リ 1922 Ph Ph Ph C O S H O CH2CH2 O 1 1 リ 1923 Ph Ph Ph C O - - - - - 0 0 リ 1924 Ph Ph Ph C O O Me O - - 0 1 リ 1925 Ph Ph Ph C O O Me S - - 0 1 リ 1926 3,5-DBP H H C O O H O CH2CH2 O 1 1 リ 1927 3,5-DBP H H C O S H O CH2CH2 O 1 1 リ 1928 3,5-DBP H H C O - - - - - 0 0 リ 1929 3,5-DBP H H C O O Me O - - 0 1 リ 1930 3,5-DBP H H C O O Me S - - 0 1 リ 1931 3,4-DBP H H C O O H O CH2CH2 O 1 1 ヌ 1932 3,4-DBP H H C O S H O CH2CH2 O 1 1 ヌ 1933 3,4-DBP H H C O - - - - - 0 0 ヌ 1934 3,4-DBP H H C O O Me O - - 0 1 ヌ 1935 3,4-DBP H H C O O Me S - - 0 1 ヌ 1936 Ph Ph Ph C O O H O CH2CH2 O 1 1 ヌ 1937 Ph Ph Ph C O S H O CH2CH2 O 1 1 ヌ 1938 Ph Ph Ph C O - - - - - 0 0 ヌ 1939 Ph Ph Ph C O O Me O - - 0 1 ヌ 1940 Ph Ph Ph C O O Me S - - 0 1 ヌ 1941 3,5-DBP H H C O O H O CH2CH2 O 1 1 ヌ 1942 3,5-DBP H H C O S H O CH2CH2 O 1 1 ヌ 1943 3,5-DBP H H C O - - - - - 0 0 ヌ 1944 3,5-DBP H H C O O Me O - - 0 1 ヌ 1945 3,5-DBP H H C O O Me S - - 0 1 ヌ 1946 3,4-DBP H H C O O H O CH2CH2 O 1 1 ル 1947 3,4-DBP H H C O S H O CH2CH2 O 1 1 ル 1948 3,4-DBP H H C O - - - - - 0 0 ル 1949 3,4-DBP H H C O O Me O - - 0 1 ル 1950 3,4-DBP H H C O O Me S - - 0 1 ル 1951 Ph Ph Ph C O O H O CH2CH2 O 1 1 ル 1952 Ph Ph Ph C O S H O CH2CH2 O 1 1 ル 1953 Ph Ph Ph C O - - - - - 0 0 ル 1954 Ph Ph Ph C O O Me O - - 0 1 ル 1955 Ph Ph Ph C O O Me S - - 0 1 ル 1956 3,5-DBP H H C O O H O CH2CH2 O 1 1 ル 1957 3,5-DBP H H C O S H O CH2CH2 O 1 1 ル 1958 3,5-DBP H H C O - - - - - 0 0 ル 1959 3,5-DBP H H C O O Me O - - 0 1 ル 1960 3,5-DBP H H C O O Me S - - 0 1 ル 1961 3,4-DBP H H C O NH Me O CH2CH2 O 1 1 1-1 1962 3,4-DBP H H C O O Ph O - - 0 1 1-1 1963 3,4-DBP H H C O O 4-ClPh O - - 0 1 1-1 1964 3,4-DBP H H C O NH 2-NH2Et O CH2CH2 O 1 1 1-1 1965 3,4-DBP H H C O NH 2-MeOEt O CH2CH2 O 1 1 1-1 1966 3,4-DBP H H C O S Me O - - 0 1 1-1 1967 3,4-DBP H H C O S H O - - 0 1 1-1 1968 3,4-DBP H H C O O H S CH2CH2 O 1 1 1-1 1969 3,4-DBP H H C O O Et O - - 0 1 1-1 1970 3,4-DBP H H C O O Et S - - 0 1 1-1 1971 3,4-DBP H H C O O Bu O - - 0 1 1-1 1972 3,4-DBP H H C O O Bu S - - 0 1 1-1 1973 3,4-DBP H H C O O H O CH2CH2 O 6 1 1-1 1974 3,4-DBP H H C O O H O CH2CH2 O 6 2 1-1 1975 3,4-DBP H H C O O H O CH2CH2 O 6 3 1-1 1976 3,4-DBP H H C O O H O CH2CH2 O 6 4 1-1 1977 3,4-DBP H H C O O H O 2-OH-PrE NH 1 1 1-1 1978 Ph Ph Ph C O NH Me O CH2CH2 O 1 1 1-1 1979 Ph Ph Ph C O O Ph O - - 0 1 1-1 1980 Ph Ph Ph C O O 4-ClPh O - - 0 1 1-1 1981 Ph Ph Ph C O NH 2-NH2Et O CH2CH2 O 1 1 1-1 1982 Ph Ph Ph C O NH 2-MeOEt O CH2CH2 O 1 1 1-1 1983 Ph Ph Ph C O S Me O - - 0 1 1-1 1984 Ph Ph Ph C O S H O - - 0 1 1-1 1985 Ph Ph Ph C O O H S CH2CH2 O 1 1 1-1 1986 Ph Ph Ph C O O Et O - - 0 1 1-1 1987 Ph Ph Ph C O O Et S - - 0 1 1-1 1988 Ph Ph Ph C O O Bu O - - 0 1 1-1 1989 Ph Ph Ph C O O Bu S - - 0 1 1-1 1990 Ph Ph Ph C O O H O CH2CH2 O 6 1 1-1 1991 Ph Ph Ph C O O H O CH2CH2 O 6 2 1-1 1992 Ph Ph Ph C O O H O CH2CH2 O 6 3 1-1 1993 Ph Ph Ph C O O H O CH2CH2 O 6 4 1-1 1994 Ph Ph Ph C O O H O 2-OH-PrE NH 1 1 1-1 1995 3,5-DBP H H C O NH Me O CH2CH2 O 1 1 1-1 1996 3,5-DBP H H C O O Ph O - - 0 1 1-1 1997 3,5-DBP H H C O O 4-ClPh O - - 0 1 1-1 1998 3,5-DBP H H C O NH 2-NH2Et O CH2CH2 O 1 1 1-1 1999 3,5-DBP H H C O NH 2-MeOEt O CH2CH2 O 1 1 1-1 2000 3,5-DBP H H C O S Me O - - 0 1 1-1 2001 3,5-DBP H H C O S H O - - 0 1 1-1 2002 3,5-DBP H H C O O H S CH2CH2 O 1 1 1-1 2003 3,5-DBP H H C O O Et O - - 0 1 1-1 2004 3,5-DBP H H C O O Et S - - 0 1 1-1 2005 3,5-DBP H H C O O Bu O - - 0 1 1-1 2006 3,5-DBP H H C O O Bu S - - 0 1 1-1 2007 3,5-DBP H H C O O H O CH2CH2 O 6 1 1-1 2008 3,5-DBP H H C O O H O CH2CH2 O 6 2 1-1 2009 3,5-DBP H H C O O H O CH2CH2 O 6 3 1-1 2010 3,5-DBP H H C O O H O CH2CH2 O 6 4 1-1 2011 3,5-DBP H H C O O H O 2-OH-PrE NH 1 1 1-1 2012 3,4-DBP H H C O NH Me O CH2CH2 O 1 1 2013 3,4-DBP H H C O O Ph O - - 0 1 2014 3,4-DBP H H C O O 4-ClPh O - - 0 1 2015 3,4-DBP H H C O NH 2-NH2Et O CH2CH2 O 1 1 2016 3,4-DBP H H C O NH 2-MeOEt O CH2CH2 O 1 1 2017 3,4-DBP H H C O S Me O - - 0 1 2018 3,4-DBP H H C O S H O - - 0 1 2019 3,4-DBP H H C O O H S CH2CH2 O 1 1 2020 3,4-DBP H H C O O Et O - - 0 1 2021 3,4-DBP H H C O O Et S - - 0 1 2022 3,4-DBP H H C O O Bu O - - 0 1 2023 3,4-DBP H H C O O Bu S - - 0 1 2024 3,4-DBP H H C O O H O CH2CH2 O 6 1 2025 3,4-DBP H H C O O H O CH2CH2 O 6 2 2026 3,4-DBP H H C O O H O CH2CH2 O 6 3 2027 3,4-DBP H H C O O H O CH2CH2 O 6 4 2028 3,4-DBP H H C O O H O 2-OH-PrE NH 1 1 2029 Ph Ph Ph C O NH Me O CH2CH2 O 1 1 2030 Ph Ph Ph C O O Ph O - - 0 1 2031 Ph Ph Ph C O O 4-ClPh O - - 0 1 2032 Ph Ph Ph C O NH 2-NH2Et O CH2CH2 O 1 1 2033 Ph Ph Ph C O NH 2-MeOEt O CH2CH2 O 1 1 2034 Ph Ph Ph C O S Me O - - 0 1 2035 Ph Ph Ph C O S H O - - 0 1 2036 Ph Ph Ph C O O H S CH2CH2 O 1 1 2037 Ph Ph Ph C O O Et O - - 0 1 2038 Ph Ph Ph C O O Et S - - 0 1 2039 Ph Ph Ph C O O Bu O - - 0 1 2040 Ph Ph Ph C O O Bu S - - 0 1 2041 Ph Ph Ph C O O H O CH2CH2 O 6 1 2042 Ph Ph Ph C O O H O CH2CH2 O 6 2 2043 Ph Ph Ph C O O H O CH2CH2 O 6 3 2044 Ph Ph Ph C O O H O CH2CH2 O 6 4 2045 Ph Ph Ph C O O H O 2-OH-PrE NH 1 1 2046 3,5-DBP H H C O NH Me O CH2CH2 O 1 1 2047 3,5-DBP H H C O O Ph O - - 0 1 2048 3,5-DBP H H C O O 4-ClPh O - - 0 1 2049 3,5-DBP H H C O NH 2-NH2Et O CH2CH2 O 1 1 2050 3,5-DBP H H C O NH 2-MeOEt O CH2CH2 O 1 1 2051 3,5-DBP H H C O S Me O - - 0 1 2052 3,5-DBP H H C O S H O - - 0 1 2053 3,5-DBP H H C O O H S CH2CH2 O 1 1 2054 3,5-DBP H H C O O Et O - - 0 1 2055 3,5-DBP H H C O O Et S - - 0 1 2056 3,5-DBP H H C O O Bu O - - 0 1 2057 3,5-DBP H H C O O Bu S - - 0 1 2058 3,5-DBP H H C O O H O CH2CH2 O 6 1 2059 3,5-DBP H H C O O H O CH2CH2 O 6 2 2060 3,5-DBP H H C O O H O CH2CH2 O 6 3 2061 3,5-DBP H H C O O H O CH2CH2 O 6 4 2062 3,5-DBP H H C O O H O 2-OH-PrE NH 1 1 2063 3,4-DBP H H C O NH Me O CH2CH2 O 1 1 3-1 2064 3,4-DBP H H C O O Ph O - - 0 1 3-1 2065 3,4-DBP H H C O O 4-ClPh O - - 0 1 3-1 2066 3,4-DBP H H C O NH 2-NH2Et O CH2CH2 O 1 1 3-1 2067 3,4-DBP H H C O NH 2-MeOEt O CH2CH2 O 1 1 3-1 2068 3,4-DBP H H C O S Me O - - 0 1 3-1 2069 3,4-DBP H H C O S H O - - 0 1 3-1 2070 3,4-DBP H H C O O H S CH2CH2 O 1 1 3-1 2071 3,4-DBP H H C O O Et O - - 0 1 3-1 2072 3,4-DBP H H C O O Et S - - 0 1 3-1 2073 3,4-DBP H H C O O Bu O - - 0 1 3-1 2074 3,4-DBP H H C O O Bu S - - 0 1 3-1 2075 3,4-DBP H H C O O H O CH2CH2 O 6 1 3-1 2076 3,4-DBP H H C O O H O CH2CH2 O 6 2 3-1 2077 3,4-DBP H H C O O H O CH2CH2 O 6 3 3-1 2078 3,4-DBP H H C O O H O CH2CH2 O 6 4 3-1 2079 3,4-DBP H H C O O H O 2-OH-PrE NH 1 1 3-1 2080 Ph Ph Ph C O NH Me O CH2CH2 O 1 1 3-1 2081 Ph Ph Ph C O O Ph O - - 0 1 3-1 2082 Ph Ph Ph C O O 4-ClPh O - - 0 1 3-1 2083 Ph Ph Ph C O NH 2-NH2Et O CH2CH2 O 1 1 3-1 2084 Ph Ph Ph C O NH 2-MeOEt O CH2CH2 O 1 1 3-1 2085 Ph Ph Ph C O S Me O - - 0 1 3-1 2086 Ph Ph Ph C O S H O - - 0 1 3-1 2087 Ph Ph Ph C O O H S CH2CH2 O 1 1 3-1 2088 Ph Ph Ph C O O Et O - - 0 1 3-1 2089 Ph Ph Ph C O O Et S - - 0 1 3-1 2090 Ph Ph Ph C O O Bu O - - 0 1 3-1 2091 Ph Ph Ph C O O Bu S - - 0 1 3-1 2092 Ph Ph Ph C O O H O CH2CH2 O 6 1 3-1 2093 Ph Ph Ph C O O H O CH2CH2 O 6 2 3-1 2094 Ph Ph Ph C O O H O CH2CH2 O 6 3 3-1 2095 Ph Ph Ph C O O H O CH2CH2 O 6 4 3-1 2096 Ph Ph Ph C O O H O 2-OH-PrE NH 1 1 3-1 2097 3,5-DBP H H C O NH Me O CH2CH2 O 1 1 3-1 2098 3,5-DBP H H C O O Ph O - - 0 1 3-1 2099 3,5-DBP H H C O O 4-ClPh O - - 0 1 3-1 2100 3,5-DBP H H C O NH 2-NH2Et O CH2CH2 O 1 1 3-1 2101 3,5-DBP H H C O NH 2-MeOEt O CH2CH2 O 1 1 3-1 2102 3,5-DBP H H C O S Me O - - 0 1 3-1 2103 3,5-DBP H H C O S H O - - 0 1 3-1 2104 3,5-DBP H H C O O H S CH2CH2 O 1 1 3-1 2105 3,5-DBP H H C O O Et O - - 0 1 3-1 2106 3,5-DBP H H C O O Et S - - 0 1 3-1 2107 3,5-DBP H H C O O Bu O - - 0 1 3-1 2108 3,5-DBP H H C O O Bu S - - 0 1 3-1 2109 3,5-DBP H H C O O H O CH2CH2 O 6 1 3-1 2110 3,5-DBP H H C O O H O CH2CH2 O 6 2 3-1 2111 3,5-DBP H H C O O H O CH2CH2 O 6 3 3-1 2112 3,5-DBP H H C O O H O CH2CH2 O 6 4 3-1 2113 3,5-DBP H H C O O H O 2-OH-PrE NH 1 1 3-1 2114 3,4-DBP H H C O NH Me O CH2CH2 O 1 1 2115 3,4-DBP H H C O O Ph O - - 0 1 2116 3,4-DBP H H C O O 4-ClPh O - - 0 1 2117 3,4-DBP H H C O NH 2-NH2Et O CH2CH2 O 1 1 2118 3,4-DBP H H C O NH 2-MeOEt O CH2CH2 O 1 1 2119 3,4-DBP H H C O S Me O - - 0 1 2120 3,4-DBP H H C O S H O - - 0 1 2121 3,4-DBP H H C O O H S CH2CH2 O 1 1 2122 3,4-DBP H H C O O Et O - - 0 1 2123 3,4-DBP H H C O O Et S - - 0 1 2124 3,4-DBP H H C O O Bu O - - 0 1 2125 3,4-DBP H H C O O Bu S - - 0 1 2126 3,4-DBP H H C O O H O CH2CH2 O 6 1 2127 3,4-DBP H H C O O H O CH2CH2 O 6 2 2128 3,4-DBP H H C O O H O CH2CH2 O 6 3 2129 3,4-DBP H H C O O H O CH2CH2 O 6 4 2130 3,4-DBP H H C O O H O 2-OH-PrE NH 1 1 2131 Ph Ph Ph C O NH Me O CH2CH2 O 1 1 2132 Ph Ph Ph C O O Ph O - - 0 1 2133 Ph Ph Ph C O O 4-ClPh O - - 0 1 2134 Ph Ph Ph C O NH 2-NH2Et O CH2CH2 O 1 1 2135 Ph Ph Ph C O NH 2-MeOEt O CH2CH2 O 1 1 2136 Ph Ph Ph C O S Me O - - 0 1 2137 Ph Ph Ph C O S H O - - 0 1 2138 Ph Ph Ph C O O H S CH2CH2 O 1 1 2139 Ph Ph Ph C O O Et O - - 0 1 2140 Ph Ph Ph C O O Et S - - 0 1 2141 Ph Ph Ph C O O Bu O - - 0 1 2142 Ph Ph Ph C O O Bu S - - 0 1 2143 Ph Ph Ph C O O H O CH2CH2 O 6 1 2144 Ph Ph Ph C O O H O CH2CH2 O 6 2 2145 Ph Ph Ph C O O H O CH2CH2 O 6 3 2146 Ph Ph Ph C O O H O CH2CH2 O 6 4 2147 Ph Ph Ph C O O H O 2-OH-PrE NH 1 1 2148 3,5-DBP H H C O NH Me O CH2CH2 O 1 1 2149 3,5-DBP H H C O O Ph O - - 0 1 2150 3,5-DBP H H C O O 4-ClPh O - - 0 1 2151 3,5-DBP H H C O NH 2-NH2Et O CH2CH2 O 1 1 2152 3,5-DBP H H C O NH 2-MeOEt O CH2CH2 O 1 1 2153 3,5-DBP H H C O S Me O - - 0 1 2154 3,5-DBP H H C O S H O - - 0 1 2155 3,5-DBP H H C O O H S CH2CH2 O 1 1 2156 3,5-DBP H H C O O Et O - - 0 1 2157 3,5-DBP H H C O O Et S - - 0 1 2158 3,5-DBP H H C O O Bu O - - 0 1 2159 3,5-DBP H H C O O Bu S - - 0 1 2160 3,5-DBP H H C O O H O CH2CH2 O 6 1 2161 3,5-DBP H H C O O H O CH2CH2 O 6 2 2162 3,5-DBP H H C O O H O CH2CH2 O 6 3 2163 3,5-DBP H H C O O H O CH2CH2 O 6 4 2164 3,5-DBP H H C O O H O 2-OH-PrE NH 1 1 2165 4-MePh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2166 4-MePh 4-MePh Ph C O O H O CH2CH2 O 1 1 1-1 2167 4-MePh 4-MePh 4-MePh C O O H O CH2CH2 O 1 1 1-1 2168 4-tBuPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2169 4-tBuPh 4-tBuPh Ph C O O H O CH2CH2 O 1 1 1-1 2170 4-tBuPh 4-tBuPh 4-tBuPh C O O H O CH2CH2 O 1 1 1-1 2171 4-NO2Ph Ph Ph C O O H O CH2CH2 O 1 1 1-1 2172 4-NO2Ph 4-NO2Ph Ph C O O H O CH2CH2 O 1 1 1-1 2173 4-FPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2174 4-FPh 4-FPh Ph C O O H O CH2CH2 O 1 1 1-1 2175 2,4-F2Ph Ph Ph C O O H O CH2CH2 O 1 1 1-1 2176 2-ClPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2177 4-ClPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2178 4-ClPh 4-ClPh Ph C O O H O CH2CH2 O 1 1 1-1 2179 4-BrPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2180 4-BrPh 4-BrPh Ph C O O H O CH2CH2 O 1 1 1-1 2181 4-IPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2182 4-tBuOPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2183 4-EtOPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2184 4-EtOPh 4-EtOPh Ph C O O H O CH2CH2 O 1 1 1-1 2185 2-BnOPh H H C O O H O CH2CH2 O 1 1 1-1 2186 4-BnOPh Ph Ph C O O H O CH2CH2 O 1 1 1-1 2187 4-BnOPh 4-BnOPh Ph C O O H O CH2CH2 O 1 1 1-1 2188 4-MeOPh 4-MeOPh 4-MeOPh C O O H O CH2CH2 O 1 1 1-1 2189 9-ANT H H C O O H O CH2CH2 O 1 1 1-1 2190 2-ANT H H C O O H O CH2CH2 O 1 1 1-1 2191 1-NAP H H C O O H O CH2CH2 O 1 1 1-1 2192 3-PhOPh H H C O O H O CH2CH2 O 1 1 1-1 2193 4-PhOPh H H C O O H O CH2CH2 O 1 1 1-1 2194 2-ANQ H H C O O H O CH2CH2 O 1 1 1-1 2195 4-PHE H H C O O H O CH2CH2 O 1 1 1-1 2196 3,4-DBP H H C O S H O CH2CH2 O 6 1 1-1 2197 3,4-DBP H H C O NH Et O CH2CH2 O 6 1 1-1 2198 3,4-DBP H H C O NH Pr O CH2CH2 O 6 1 1-1 2199 3,4-DBP H H C O NH 2-NH2Et O CH2CH2 O 6 1 1-1 2200 3,4-DBP H H C O O H O CH2CH2 O 2 1 1-1 2201 3,4-DBP H H C O S H O CH2CH2 O 2 1 1-1 2202 3,4-DBP H H C O O 2-NO2Ph O - - 0 1 1-1 2203 3,4-DBP H H C O O 4-NO2Ph O - - 0 1 1-1 2204 3,4-DBP H H C O O 2-FPh O - - 0 1 1-1 2205 3,4-DBP H H C O O 2-BrPh O - - 0 1 1-1 2206 3,4-DBP H H C O O 2-IPh O - - 0 1 1-1 2207 3,4-DBP H H C O O 4-MeOPh O - - 0 1 1-1 2208 3,4-DBP H H C O O 4-MeSPh O - - 0 1 1-1 2209 3,4-DBP H H C O O 4-EtOPh O - - 0 1 1-1 2210 3,4-DBP H H C O O H O (CH2)3 O 1 1 1-1 2211 3,4-DBP H H C O O H O (CH2)4 O 1 1 1-1 2212 3,4-DBP H H C O O H O (CH2)5 O 1 1 1-1 2213 3,4-DBP H H C O O H O (CH2)6 O 1 1 1-1 2214 3,4-DBP H H C O O H O (CH2)7 O 1 1 1-1 2215 3,4-DBP H H C O O H O (CH2)8 O 1 1 1-1 2216 3,4-DBP H H C O O H O (CH2)9 O 1 1 1-1 2217 3,4-DBP H H C O O H O (CH2)10 O 1 1 1-1 2218 3,4-DBP H H C O O H O CH2CH(CH3) O 1 1 1-1 2219 3,4-DBP H H C O O H O 1-Me-PrE O 1 1 1-1 2220 3,4-DBP H H C O O H O 2-Me-BuE O 1 1 1-1 2221 3,4-DBP H H C O S H O (CH2)3 O 1 1 1-1 2222 3,4-DBP H H C O S H O (CH2)4 O 1 1 1-1 2223 3,4-DBP H H C O S H O (CH2)5 O 1 1 1-1 2224 3,4-DBP H H C O S H O (CH2)6 O 1 1 1-1 2225 3,4-DBP H H C O S H O (CH2)7 O 1 1 1-1 2226 3,4-DBP H H C O S H O (CH2)8 O 1 1 1-1 2227 3,4-DBP H H C O S H O (CH2)9 O 1 1 1-1 2228 3,4-DBP H H C O S H O (CH2)10 O 1 1 1-1 2229 3,4-DBP H H C O S H O CH2CH(CH3) O 1 1 1-1 2230 3,4-DBP H H C O S H O 1-Me-PrE O 1 1 1-1 2231 3,4-DBP H H C O S H O 2-Me-BuE O 1 1 1-1 2232 3,4-DBP H H C O NH Ph O CH2CH2 O 1 1 1-1 2233 3,4-DBP H H C O NH 2-ClPh O CH2CH2 O 1 1 1-1 2234 3,4-DBP H H C O NH Me O (CH2)3 O 1 1 1-1 2235 3,4-DBP H H C O NH Pr O (CH2)3 O 1 1 1-1 2236 3,4-DBP H H C O NH 2-NH2Et O (CH2)3 O 1 1 1-1 2237 3,4-DBP H H C O NH 2-MeOEt O (CH2)3 O 1 1 1-1 2238 3,4-DBP H H C O NH Ph O (CH2)3 O 1 1 1-1 2239 3,4-DBP H H C O NH 2-ClPh O (CH2)3 O 1 1 1-1 2240 3,4-DBP H H C O NH Pr O (CH2)4 O 1 1 1-1 2241 3,4-DBP H H C O NH Pr O (CH2)5 O 1 1 1-1 2242 3,4-DBP H H C O NH Pr O (CH2)6 O 1 1 1-1 2243 3,4-DBP H H C O NH Pr O (CH2)7 O 1 1 1-1 2244 3,4-DBP H H C O NH Pr O (CH2)8 O 1 1 1-1 2245 3,4-DBP H H C O NH Pr O (CH2)9 O 1 1 1-1 2246 3,4-DBP H H C O NH Pr O (CH2)10 O 1 1 1-1 2247 3,4-DBP H H C O NH Pr O CH2CH(CH3) O 1 1 1-1 2248 3,4-DBP H H C O NH Pr O 1-Me-PrE O 1 1 1-1 2249 3,4-DBP H H C O NH Pr O 2-Me-BuE O 1 1 1-1 2250 Ph Ph Ph C NH O H O CH2CH2 O 6 1 1-1 2251 3,4-DBP H H C O O H O CH2CH2 O 1 1 ヲ 2252 3,4-DBP H H C O S H O CH2CH2 O 1 1 ヲ 2253 3,4-DBP H H C O - - - - - 0 0 ヲ 2254 3,4-DBP H H C O O Me O - - 0 1 ヲ 2255 3,4-DBP H H C O O Me S - - 0 1 ヲ 2256 Ph Ph Ph C O O H O CH2CH2 O 1 1 ヲ 2257 Ph Ph Ph C O S H O CH2CH2 O 1 1 ヲ 2258 Ph Ph Ph C O - - - - - 0 0 ヲ 2259 Ph Ph Ph C O O Me O - - 0 1 ヲ 2260 Ph Ph Ph C O O Me S - - 0 1 ヲ 2261 3,5-DBP H H C O O H O CH2CH2 O 1 1 ヲ 2262 3,5-DBP H H C O S H O CH2CH2 O 1 1 ヲ 2263 3,5-DBP H H C O - - - - - 0 0 ヲ 2264 3,5-DBP H H C O O Me O - - 0 1 ヲ 2265 3,5-DBP H H C O O Me S - - 0 1 ヲ 2266 3,4-DBP H H C O O H O CH2CH2 O 1 1 ワ 2267 3,4-DBP H H C O S H O CH2CH2 O 1 1 ワ 2268 3,4-DBP H H C O - - - - - 0 0 ワ 2269 3,4-DBP H H C O O Me O - - 0 1 ワ 2270 3,4-DBP H H C O O Me S - - 0 1 ワ 2271 Ph Ph Ph C O O H O CH2CH2 O 1 1 ワ 2272 Ph Ph Ph C O S H O CH2CH2 O 1 1 ワ 2273 Ph Ph Ph C O - - - - - 0 0 ワ 2274 Ph Ph Ph C O O Me O - - 0 1 ワ 2275 Ph Ph Ph C O O Me S - - 0 1 ワ 2276 3,5-DBP H H C O O H O CH2CH2 O 1 1 ワ 2277 3,5-DBP H H C O S H O CH2CH2 O 1 1 ワ 2278 3,5-DBP H H C O - - - - - 0 0 ワ 2279 3,5-DBP H H C O O Me O - - 0 1 ワ 2280 3,5-DBP H H C O O Me S - - 0 1 ワ 2281 3,4-DBP H H C O O H O CH2CH2 O 1 1 カ 2282 3,4-DBP H H C O S H O CH2CH2 O 1 1 カ 2283 3,4-DBP H H C O - - - - - 0 0 カ 2284 3,4-DBP H H C O O Me O - - 0 1 カ 2285 3,4-DBP H H C O O Me S - - 0 1 カ 2286 Ph Ph Ph C O O H O CH2CH2 O 1 1 カ 2287 Ph Ph Ph C O S H O CH2CH2 O 1 1 カ 2288 Ph Ph Ph C O - - - - - 0 0 カ 2289 Ph Ph Ph C O O Me O - - 0 1 カ 2290 Ph Ph Ph C O O Me S - - 0 1 カ 2291 3,5-DBP H H C O O H O CH2CH2 O 1 1 カ 2292 3,5-DBP H H C O S H O CH2CH2 O 1 1 カ 2293 3,5-DBP H H C O - - - - - 0 0 カ 2294 3,5-DBP H H C O O Me O - - 0 1 カ 2295 3,5-DBP H H C O O Me S - - 0 1 カ 2296 3,4-DBP H H C O O H O CH2CH2 O 1 1 ヨ 2297 3,4-DBP H H C O S H O CH2CH2 O 1 1 ヨ 2298 3,4-DBP H H C O - - - - - 0 0 ヨ 2299 3,4-DBP H H C O O Me O - - 0 1 ヨ 2300 3,4-DBP H H C O O Me S - - 0 1 ヨ 2301 Ph Ph Ph C O O H O CH2CH2 O 1 1 ヨ 2302 Ph Ph Ph C O S H O CH2CH2 O 1 1 ヨ 2303 Ph Ph Ph C O - - - - - 0 0 ヨ 2304 Ph Ph Ph C O O Me O - - 0 1 ヨ 2305 Ph Ph Ph C O O Me S - - 0 1 ヨ 2306 3,5-DBP H H C O O H O CH2CH2 O 1 1 ヨ 2307 3,5-DBP H H C O S H O CH2CH2 O 1 1 ヨ 2308 3,5-DBP H H C O - 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1 1 c-1 2577 3,5-DBP H H C O O H O CH2CH2 O 1 1 c-1 2578 3,5-DBP H H C O S H O CH2CH2 O 1 1 c-1 2579 3,5-DBP H H C O - - - - - 0 0 c-1 2580 3,5-DBP H H C O O Me O - - 0 1 c-1 2581 3,5-DBP H H C O O Me S - - 0 1 c-1 2582 3,5-DBP H H C O O 2-ClPh O - - 0 1 c-1 2583 3,5-DBP H H C O CH2 H O - - 0 1 c-1 2584 3,5-DBP H H C O CH2 H S - - 0 1 c-1 2585 3,5-DBP H H C O PhE H O - - 0 1 c-1 2586 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 c-1 2587 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 c-1 2588 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 c-1 2589 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 c-1 2590 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 c-1 2591 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 c-1 2592 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 c-1 2593 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 c-1 2594 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 c-1 2595 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 c-1 2596 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 c-1 2597 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 c-1 2598 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 c-1 2599 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 c-1 2600 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 c-1 2601 4-MeOPh Ph Ph C O - - - - - 0 0 c-1 2602 4-MeOPh Ph Ph C O O Me O - - 0 1 c-1 2603 4-MeOPh Ph Ph C O O Me S - - 0 1 c-1 2604 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 c-1 2605 4-MeOPh Ph Ph C O CH2 H O - - 0 1 c-1 2606 4-MeOPh Ph Ph C O CH2 H S - - 0 1 c-1 2607 4-MeOPh Ph Ph C O PhE H O - - 0 1 c-1 2608 4-MeOPh Ph Ph C O NH Pr O CH2CH2 O 1 1 c-1 2609 4-MeOPh Ph Ph C O O Me NH (CH2)3 - 1 1 c-1 2610 tBu Ph Ph Si O O H O CH2CH2 O 1 1 c-1 2611 tBu Ph Ph Si O S H O CH2CH2 O 1 1 c-1 2612 tBu Ph Ph Si O - - - - - 0 0 c-1 2613 tBu Ph Ph Si O O Me O - - 0 1 c-1 2614 tBu Ph Ph Si O O Me S - - 0 1 c-1 2615 tBu Ph Ph Si O O 2-ClPh O - - 0 1 c-1 2616 tBu Ph Ph Si O CH2 H O - - 0 1 c-1 2617 tBu Ph Ph Si O CH2 H S - - 0 1 c-1 2618 tBu Ph Ph Si O PhE H O - - 0 1 c-1 2619 tBu Ph Ph Si O NH Pr O CH2CH2 O 1 1 c-1 2620 tBu Ph Ph Si O O Me NH (CH2)3 - 1 1 c-1 2621 Ph Ph Ph C S O H O CH2CH2 O 1 1 c-1 2622 Ph Ph Ph C S S H O CH2CH2 O 1 1 c-1 2623 Ph Ph Ph C S - - - - - 0 0 c-1 2624 Ph Ph Ph C S O Me O - - 0 1 c-1 2625 Ph Ph Ph C S O Me S - - 0 1 c-1 2626 Ph Ph Ph C S O 2-ClPh O - - 0 1 c-1 2627 Ph Ph Ph C S CH2 H O - - 0 1 c-1 2628 Ph Ph Ph C S CH2 H S - - 0 1 c-1 2629 Ph Ph Ph C S PhE H O - - 0 1 c-1 2630 Ph Ph Ph C S NH Pr O CH2CH2 O 1 1 c-1 2631 Ph Ph Ph C S O Me NH (CH2)3 - 1 1 c-1 2632 4-BnOPh H H C O O H O CH2CH2 O 1 1 c-1 2633 4-BnOPh H H C O S H O CH2CH2 O 1 1 c-1 2634 4-BnOPh H H C O - - - - - 0 0 c-1 2635 4-BnOPh H H C O O Me O - - 0 1 c-1 2636 4-BnOPh H H C O O Me S - - 0 1 c-1 2637 4-BnOPh H H C O O 2-ClPh O - - 0 1 c-1 2638 4-BnOPh H H C O CH2 H O - - 0 1 c-1 2639 4-BnOPh H H C O CH2 H S - - 0 1 c-1 2640 4-BnOPh H H C O PhE H O - - 0 1 c-1 2641 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 c-1 2642 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 c-1 2643 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 c-1 2644 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 c-1 2645 Ph Xanthen-9-yl O - - - - - 0 0 c-1 2646 Ph Xanthen-9-yl O O Me O - - 0 1 c-1 2647 Ph Xanthen-9-yl O O Me S - 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- 0 1 d-1 2696 3,5-DBP H H C O NH Pr O CH2CH2 O 1 1 d-1 2697 3,5-DBP H H C O O Me NH (CH2)3 - 1 1 d-1 2698 4-MeOPh 4-MeOPh Ph C O O H O CH2CH2 O 1 1 d-1 2699 4-MeOPh 4-MeOPh Ph C O S H O CH2CH2 O 1 1 d-1 2700 4-MeOPh 4-MeOPh Ph C O - - - - - 0 0 d-1 2701 4-MeOPh 4-MeOPh Ph C O O Me O - - 0 1 d-1 2702 4-MeOPh 4-MeOPh Ph C O O Me S - - 0 1 d-1 2703 4-MeOPh 4-MeOPh Ph C O O 2-ClPh O - - 0 1 d-1 2704 4-MeOPh 4-MeOPh Ph C O CH2 H O - - 0 1 d-1 2705 4-MeOPh 4-MeOPh Ph C O CH2 H S - - 0 1 d-1 2706 4-MeOPh 4-MeOPh Ph C O PhE H O - - 0 1 d-1 2707 4-MeOPh 4-MeOPh Ph C O NH Pr O CH2CH2 O 1 1 d-1 2708 4-MeOPh 4-MeOPh Ph C O O Me NH (CH2)3 - 1 1 d-1 2709 4-MeOPh Ph Ph C O O H O CH2CH2 O 1 1 d-1 2710 4-MeOPh Ph Ph C O S H O CH2CH2 O 1 1 d-1 2711 4-MeOPh Ph Ph C O - - - - - 0 0 d-1 2712 4-MeOPh Ph Ph C O O Me O - - 0 1 d-1 2713 4-MeOPh Ph Ph C O O Me S - - 0 1 d-1 2714 4-MeOPh Ph Ph C O O 2-ClPh O - - 0 1 d-1 2715 4-MeOPh Ph Ph C O CH2 H O - - 0 1 d-1 2716 4-MeOPh Ph Ph C O CH2 H S - - 0 1 d-1 2717 4-MeOPh Ph Ph C O PhE H O - 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- - - - 0 0 d-1 2745 4-BnOPh H H C O O Me O - - 0 1 d-1 2746 4-BnOPh H H C O O Me S - - 0 1 d-1 2747 4-BnOPh H H C O O 2-ClPh O - - 0 1 d-1 2748 4-BnOPh H H C O CH2 H O - - 0 1 d-1 2749 4-BnOPh H H C O CH2 H S - - 0 1 d-1 2750 4-BnOPh H H C O PhE H O - - 0 1 d-1 2751 4-BnOPh H H C O NH Pr O CH2CH2 O 1 1 d-1 2752 4-BnOPh H H C O O Me NH (CH2)3 - 1 1 d-1 2753 Ph Xanthen-9-yl O O H O CH2CH2 O 1 1 d-1 2754 Ph Xanthen-9-yl O S H O CH2CH2 O 1 1 d-1 2755 Ph Xanthen-9-yl O - - - - - 0 0 d-1 2756 Ph Xanthen-9-yl O O Me O - - 0 1 d-1 2757 Ph Xanthen-9-yl O O Me S - - 0 1 d-1 2758 Ph Xanthen-9-yl O O 2-ClPh O - - 0 1 d-1 2759 Ph Xanthen-9-yl O CH2 H O - - 0 1 d-1 2760 Ph Xanthen-9-yl O CH2 H S - - 0 1 d-1 2761 Ph Xanthen-9-yl O PhE H O - - 0 1 d-1 2762 Ph Xanthen-9-yl O NH Pr O CH2CH2 O 1 1 d-1 2763 Ph Xanthen-9-yl O O Me NH (CH2)3 - 1 1 d-1 2764 Ph Fluoren-9-yl O O H O CH2CH2 O 1 1 d-1 2765 Ph Fluoren-9-yl O S H O CH2CH2 O 1 1 d-1 2766 Ph Fluoren-9-yl O - - - - - 0 0 d-1 2767 Ph Fluoren-9-yl O O Me O - - 0 1 d-1 2768 Ph Fluoren-9-yl O O Me S - - 0 1 d-1 2769 Ph Fluoren-9-yl O O 2-ClPh O - - 0 1 d-1 2770 Ph Fluoren-9-yl O CH2 H O - - 0 1 d-1 2771 Ph Fluoren-9-yl O CH2 H S - - 0 1 d-1 2772 Ph Fluoren-9-yl O PhE H O - - 0 1 d-1 2773 Ph Fluoren-9-yl O NH Pr O CH2CH2 O 1 1 d-1 2774 Ph Fluoren-9-yl O O Me NH (CH2)3 - 1 1 d-1 2775 3,4-DBP H H C S O H O CH2CH2 O 1 1 1-1 2776 3,4-DBP H H C S S H O CH2CH2 O 1 1 1-1 2777 3,4-DBP H H C S - - - - - 0 0 1-1 2778 3,4-DBP H H C S O Me O - - 0 1 1-1 2779 3,4-DBP H H C S O Me S - - 0 1 1-1 2780 3,4-DBP H H C S O 2-ClPh O - - 0 1 1-1 2781 3,4-DBP H H C S CH2 H O - - 0 1 1-1 2782 3,4-DBP H H C S CH2 H S - - 0 1 1-1 2783 3,4-DBP H H C S PhE H O - - 0 1 1-1 2784 3,4-DBP H H C S NH Pr O CH2CH2 O 1 1 1-1 2785 3,4-DBP H H C S O Me NH (CH2)3 - 1 1 1-1 2786 9-ANT H H C S O H O CH2CH2 O 1 1 1-1 2787 9-ANT H H C S S H O CH2CH2 O 1 1 1-1 2788 9-ANT H H C S - - - - - 0 0 1-1 2789 9-ANT H H C S O Me O - - 0 1 1-1 2790 9-ANT H H C S O Me S - - 0 1 1-1 2791 9-ANT H H C S O 2-ClPh O - 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- 0 1 1-1 2817 BDBBP H H C S NH Pr O CH2CH2 O 1 1 1-1 2818 BDBBP H H C S O Me NH (CH2)3 - 1 1 1-1 2819 3,4-DBP H H C S O H O CH2CH2 O 1 1 c-1 2820 3,4-DBP H H C S S H O CH2CH2 O 1 1 c-1 2821 3,4-DBP H H C S - - - - - 0 0 c-1 2822 3,4-DBP H H C S O Me O - - 0 1 c-1 2823 3,4-DBP H H C S O Me S - - 0 1 c-1 2824 3,4-DBP H H C S O 2-ClPh O - - 0 1 c-1 2825 3,4-DBP H H C S CH2 H O - - 0 1 c-1 2826 3,4-DBP H H C S CH2 H S - - 0 1 c-1 2827 3,4-DBP H H C S PhE H O - - 0 1 c-1 2828 3,4-DBP H H C S NH Pr O CH2CH2 O 1 1 c-1 2829 3,4-DBP H H C S O Me NH (CH2)3 - 1 1 c-1 2830 9-ANT H H C S O H O CH2CH2 O 1 1 c-1 2831 9-ANT H H C S S H O CH2CH2 O 1 1 c-1 2832 9-ANT H H C S - - - - - 0 0 c-1 2833 9-ANT H H C S O Me O - - 0 1 c-1 2834 9-ANT H H C S O Me S - - 0 1 c-1 2835 9-ANT H H C S O 2-ClPh O - - 0 1 c-1 2836 9-ANT H H C S CH2 H O - - 0 1 c-1 2837 9-ANT H H C S CH2 H S - - 0 1 c-1 2838 9-ANT H H C S PhE H O - - 0 1 c-1 2839 9-ANT H H C S NH Pr O CH2CH2 O 1 1 c-1 2840 9-ANT H H C S O Me NH (CH2)3 - 1 1 c-1 2841 2-NAP H H C S O H O CH2CH2 O 1 1 c-1 2842 2-NAP H H C S S H O CH2CH2 O 1 1 c-1 2843 2-NAP H H C S - - - - - 0 0 c-1 2844 2-NAP H H C S O Me O - - 0 1 c-1 2845 2-NAP H H C S O Me S - - 0 1 c-1 2846 2-NAP H H C S O 2-ClPh O - - 0 1 c-1 2847 2-NAP H H C S CH2 H O - - 0 1 c-1 2848 2-NAP H H C S CH2 H S - - 0 1 c-1 2849 2-NAP H H C S PhE H O - - 0 1 c-1 2850 2-NAP H H C S NH Pr O CH2CH2 O 1 1 c-1 2851 2-NAP H H C S O Me NH (CH2)3 - 1 1 c-1 2852 BDBBP H H C S O H O CH2CH2 O 1 1 c-1 2853 BDBBP H H C S S H O CH2CH2 O 1 1 c-1 2854 BDBBP H H C S - - - - - 0 0 c-1 2855 BDBBP H H C S O Me O - - 0 1 c-1 2856 BDBBP H H C S O Me S - - 0 1 c-1 2857 BDBBP H H C S O 2-ClPh O - - 0 1 c-1 2858 BDBBP H H C S CH2 H O - - 0 1 c-1 2859 BDBBP H H C S CH2 H S - - 0 1 c-1 2860 BDBBP H H C S PhE H O - - 0 1 c-1 2861 BDBBP H H C S NH Pr O CH2CH2 O 1 1 c-1 2862 BDBBP H H C S O Me NH (CH2)3 - 1 1 c-1 2863 3,4-DBP H H C S O H O CH2CH2 O 1 1 d-1 2864 3,4-DBP H H C S S H O CH2CH2 O 1 1 d-1 2865 3,4-DBP H H C S - - - - - 0 0 d-1 2866 3,4-DBP H H C S O Me O - - 0 1 d-1 2867 3,4-DBP H H C S O Me S - - 0 1 d-1 2868 3,4-DBP H H C S O 2-ClPh O - - 0 1 d-1 2869 3,4-DBP H H C S CH2 H O - - 0 1 d-1 2870 3,4-DBP H H C S CH2 H S - - 0 1 d-1 2871 3,4-DBP H H C S PhE H O - - 0 1 d-1 2872 3,4-DBP H H C S NH Pr O CH2CH2 O 1 1 d-1 2873 3,4-DBP H H C S O Me NH (CH2)3 - 1 1 d-1 2874 9-ANT H H C S O H O CH2CH2 O 1 1 d-1 2875 9-ANT H H C S S H O CH2CH2 O 1 1 d-1 2876 9-ANT H H C S - - - - - 0 0 d-1 2877 9-ANT H H C S O Me O - - 0 1 d-1 2878 9-ANT H H C S O Me S - - 0 1 d-1 2879 9-ANT H H C S O 2-ClPh O - - 0 1 d-1 2880 9-ANT H H C S CH2 H O - - 0 1 d-1 2881 9-ANT H H C S CH2 H S - - 0 1 d-1 2882 9-ANT H H C S PhE H O - - 0 1 d-1 2883 9-ANT H H C S NH Pr O CH2CH2 O 1 1 d-1 2884 9-ANT H H C S O Me NH (CH2)3 - 1 1 d-1 2885 2-NAP H H C S O H O CH2CH2 O 1 1 d-1 2886 2-NAP H H C S S H O CH2CH2 O 1 1 d-1 2887 2-NAP H H C S - - - - - 0 0 d-1 2888 2-NAP H H C S O Me O - - 0 1 d-1 2889 2-NAP H H C S O Me S - - 0 1 d-1 2890 2-NAP H H C S O 2-ClPh O - - 0 1 d-1 2891 2-NAP H H C S CH2 H O - - 0 1 d-1 2892 2-NAP H H C S CH2 H S - - 0 1 d-1 2893 2-NAP H H C S PhE H O - - 0 1 d-1 2894 2-NAP H H C S NH Pr O CH2CH2 O 1 1 d-1 2895 2-NAP H H C S O Me NH (CH2)3 - 1 1 d-1 2896 BDBBP H H C S O H O CH2CH2 O 1 1 d-1 2897 BDBBP H H C S S H O CH2CH2 O 1 1 d-1 2898 BDBBP H H C S - - - - - 0 0 d-1 2899 BDBBP H H C S O Me O - - 0 1 d-1 2900 BDBBP H H C S O Me S - - 0 1 d-1 2901 BDBBP H H C S O 2-ClPh O - - 0 1 d-1 2902 BDBBP H H C S CH2 H O - - 0 1 d-1 2903 BDBBP H H C S CH2 H S - - 0 1 d-1 2904 BDBBP H H C S PhE H O - - 0 1 d-1 2905 BDBBP H H C S NH Pr O CH2CH2 O 1 1 d-1 2906 BDBBP H H C S O Me NH (CH2)3 - 1 1 d-1 2907 3,4-DBP H H C O O H O CH2CH2 O 1 1 ｅ 2908 3,4-DBP H H C O S H O CH2CH2 O 1 1 ｅ 2909 3,4-DBP H H C O - - - - - 0 0 ｅ 2910 3,4-DBP H H C O O Me O - - 0 1 ｅ 2911 3,4-DBP H H C O O Me S - - 0 1 ｅ 2912 3,4-DBP H H C O O 2-ClPh O - - 0 1 ｅ 2913 3,4-DBP H H C O CH2 H O - - 0 1 ｅ 2914 3,4-DBP H H C O CH2 H S - - 0 1 ｅ 2915 3,4-DBP H H C O PhE H O - - 0 1 ｅ 2916 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ｅ 2917 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ｅ 2918 3,4-DBP H H C O O H O CH2CH2 O 1 1 ｆ 2919 3,4-DBP H H C O S H O CH2CH2 O 1 1 ｆ 2920 3,4-DBP H H C O - - - - - 0 0 ｆ 2921 3,4-DBP H H C O O Me O - - 0 1 ｆ 2922 3,4-DBP H H C O O Me S - - 0 1 ｆ 2923 3,4-DBP H H C O O 2-ClPh O - - 0 1 ｆ 2924 3,4-DBP H H C O CH2 H O - - 0 1 ｆ 2925 3,4-DBP H H C O CH2 H S - - 0 1 ｆ 2926 3,4-DBP H H C O PhE H O - - 0 1 ｆ 2927 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ｆ 2928 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ｆ 2929 3,4-DBP H H C O O H O CH2CH2 O 1 1 ｇ 2930 3,4-DBP H H C O S H O CH2CH2 O 1 1 ｇ 2931 3,4-DBP H H C O - - - - - 0 0 ｇ 2932 3,4-DBP H H C O O Me O - - 0 1 ｇ 2933 3,4-DBP H H C O O Me S - - 0 1 ｇ 2934 3,4-DBP H H C O O 2-ClPh O - - 0 1 ｇ 2935 3,4-DBP H H C O CH2 H O - - 0 1 ｇ 2936 3,4-DBP H H C O CH2 H S - - 0 1 ｇ 2937 3,4-DBP H H C O PhE H O - - 0 1 ｇ 2938 3,4-DBP H H C O NH Pr O CH2CH2 O 1 1 ｇ 2939 3,4-DBP H H C O O Me NH (CH2)3 - 1 1 ｇ 2940 3,4-DBP H H C O O H O CH2CH2 O 1 1 1-2 2941 3,4-DBP H H C O S H O CH2CH2 O 1 1 1-2 2942 3,4-DBP H H C O - 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- - - - 0 0 1-15 3218 tBu Ph Ph Si O O Me O - - 0 1 1-15 3219 tBu Ph Ph Si O O Me S - - 0 1 1-15 3220 3,4-DBP H H C O O H O CH2CH2 O 1 1 3-2 3221 3,4-DBP H H C O S H O CH2CH2 O 1 1 3-2 3222 3,4-DBP H H C O - - - - - 0 0 3-2 3223 3,4-DBP H H C O O Me O - - 0 1 3-2 3224 3,4-DBP H H C O O Me S - - 0 1 3-2 3225 Ph Ph Ph C O O H O CH2CH2 O 1 1 3-2 3226 Ph Ph Ph C O S H O CH2CH2 O 1 1 3-2 3227 Ph Ph Ph C O - - - - - 0 0 3-2 3228 Ph Ph Ph C O O Me O - - 0 1 3-2 3229 Ph Ph Ph C O O Me S - - 0 1 3-2 3230 3,5-DBP H H C O O H O CH2CH2 O 1 1 3-2 3231 3,5-DBP H H C O S H O CH2CH2 O 1 1 3-2 3232 3,5-DBP H H C O - - - - - 0 0 3-2 3233 3,5-DBP H H C O O Me O - - 0 1 3-2 3234 3,5-DBP H H C O O Me S - - 0 1 3-2 3235 tBu Ph Ph Si O O H O CH2CH2 O 1 1 3-2 3236 tBu Ph Ph Si O S H O CH2CH2 O 1 1 3-2 3237 tBu Ph Ph Si O - - - - - 0 0 3-2 3238 tBu Ph Ph Si O O Me O - - 0 1 3-2 3239 tBu Ph Ph Si O O Me S - - 0 1 3-2 3240 3,4-DBP H H C O O H O CH2CH2 O 1 1 3-3 3241 3,4-DBP H H C O S H O CH2CH2 O 1 1 3-3 3242 3,4-DBP H H C O - - - - - 0 0 3-3 3243 3,4-DBP H H C O O Me O - - 0 1 3-3 3244 3,4-DBP H H C O O Me S - - 0 1 3-3 3245 Ph Ph Ph C O O H O CH2CH2 O 1 1 3-3 3246 Ph Ph Ph C O S H O CH2CH2 O 1 1 3-3 3247 Ph Ph Ph C O - - - - - 0 0 3-3 3248 Ph Ph Ph C O O Me O - - 0 1 3-3 3249 Ph Ph Ph C O O Me S - - 0 1 3-3 3250 3,5-DBP H H C O O H O CH2CH2 O 1 1 3-3 3251 3,5-DBP H H C O S H O CH2CH2 O 1 1 3-3 3252 3,5-DBP H H C O - - - - - 0 0 3-3 3253 3,5-DBP H H C O O Me O - - 0 1 3-3 3254 3,5-DBP H H C O O Me S - - 0 1 3-3 3255 tBu Ph Ph Si O O H O CH2CH2 O 1 1 3-3 3256 tBu Ph Ph Si O S H O CH2CH2 O 1 1 3-3 3257 tBu Ph Ph Si O - - - - - 0 0 3-3 3258 tBu Ph Ph Si O O Me O - - 0 1 3-3 3259 tBu Ph Ph Si O O Me S - - 0 1 3-3 3260 3,4-DBP H H C O O H O CH2CH2 O 1 1 a-2 3261 3,4-DBP H H C O S H O CH2CH2 O 1 1 a-2 3262 3,4-DBP H H C O - - - - - 0 0 a-2 3263 3,4-DBP H H C O O Me O - - 0 1 a-2 3264 3,4-DBP H H C O O Me S - - 0 1 a-2 3265 Ph Ph Ph C O O H O CH2CH2 O 1 1 a-2 3266 Ph Ph Ph C O S H O CH2CH2 O 1 1 a-2 3267 Ph Ph Ph C O - - - - - 0 0 a-2 3268 Ph Ph Ph C O O Me O - - 0 1 a-2 3269 Ph Ph Ph C O O Me S - - 0 1 a-2 3270 3,5-DBP H H C O O H O CH2CH2 O 1 1 a-2 3271 3,5-DBP H H C O S H O CH2CH2 O 1 1 a-2 3272 3,5-DBP H H C O - - - - - 0 0 a-2 3273 3,5-DBP H H C O O Me O - - 0 1 a-2 3274 3,5-DBP H H C O O Me S - - 0 1 a-2 3275 tBu Ph Ph Si O O H O CH2CH2 O 1 1 a-2 3276 tBu Ph Ph Si O S H O CH2CH2 O 1 1 a-2 3277 tBu Ph Ph Si O - - - - - 0 0 a-2 3278 tBu Ph Ph Si O O Me O - - 0 1 a-2 3279 tBu Ph Ph Si O O Me S - - 0 1 a-2 3280 3,4-DBP H H C O O H O CH2CH2 O 1 1 a-3 3281 3,4-DBP H H C O S H O CH2CH2 O 1 1 a-3 3282 3,4-DBP H H C O - - - - - 0 0 a-3 3283 3,4-DBP H H C O O Me O - - 0 1 a-3 3284 3,4-DBP H H C O O Me S - - 0 1 a-3 3285 Ph Ph Ph C O O H O CH2CH2 O 1 1 a-3 3286 Ph Ph Ph C O S H O CH2CH2 O 1 1 a-3 3287 Ph Ph Ph C O - - - - - 0 0 a-3 3288 Ph Ph Ph C O O Me O - - 0 1 a-3 3289 Ph Ph Ph C O O Me S - - 0 1 a-3 3290 3,5-DBP H H C O O H O CH2CH2 O 1 1 a-3 3291 3,5-DBP H H C O S H O CH2CH2 O 1 1 a-3 3292 3,5-DBP H H C O - - - - - 0 0 a-3 3293 3,5-DBP H H C O O Me O - - 0 1 a-3 3294 3,5-DBP H H C O O Me S - - 0 1 a-3 3295 tBu Ph Ph Si O O H O CH2CH2 O 1 1 a-3 3296 tBu Ph Ph Si O S H O CH2CH2 O 1 1 a-3 3297 tBu Ph Ph Si O - - - - - 0 0 a-3 3298 tBu Ph Ph Si O O Me O - - 0 1 a-3 3299 tBu Ph Ph Si O O Me S - - 0 1 a-3 3300 3,4-DBP H H C O O H O CH2CH2 O 1 1 b-2 3301 3,4-DBP H H C O S H O CH2CH2 O 1 1 b-2 3302 3,4-DBP H H C O - - - - - 0 0 b-2 3303 3,4-DBP H H C O O Me O - - 0 1 b-2 3304 3,4-DBP H H C O O Me S - - 0 1 b-2 3305 Ph Ph Ph C O O H O CH2CH2 O 1 1 b-2 3306 Ph Ph Ph C O S H O CH2CH2 O 1 1 b-2 3307 Ph Ph Ph C O - - - - - 0 0 b-2 3308 Ph Ph Ph C O O Me O - - 0 1 b-2 3309 Ph Ph Ph C O O Me S - - 0 1 b-2 3310 3,5-DBP H H C O O H O CH2CH2 O 1 1 b-2 3311 3,5-DBP H H C O S H O CH2CH2 O 1 1 b-2 3312 3,5-DBP H H C O - - - - - 0 0 b-2 3313 3,5-DBP H H C O O Me O - - 0 1 b-2 3314 3,5-DBP H H C O O Me S - - 0 1 b-2 3315 tBu Ph Ph Si O O H O CH2CH2 O 1 1 b-2 3316 tBu Ph Ph Si O S H O CH2CH2 O 1 1 b-2 3317 tBu Ph Ph Si O - - - - - 0 0 b-2 3318 tBu Ph Ph Si O O Me O - - 0 1 b-2 3319 tBu Ph Ph Si O O Me S - - 0 1 b-2 3320 3,4-DBP H H C O O H O CH2CH2 O 1 1 b-3 3321 3,4-DBP H H C O S H O CH2CH2 O 1 1 b-3 3322 3,4-DBP H H C O - - - - - 0 0 b-3 3323 3,4-DBP H H C O O Me O - - 0 1 b-3 3324 3,4-DBP H H C O O Me S - - 0 1 b-3 3325 Ph Ph Ph C O O H O CH2CH2 O 1 1 b-3 3326 Ph Ph Ph C O S H O CH2CH2 O 1 1 b-3 3327 Ph Ph Ph C O - - - - - 0 0 b-3 3328 Ph Ph Ph C O O Me O - - 0 1 b-3 3329 Ph Ph Ph C O O Me S - - 0 1 b-3 3330 3,5-DBP H H C O O H O CH2CH2 O 1 1 b-3 3331 3,5-DBP H H C O S H O CH2CH2 O 1 1 b-3 3332 3,5-DBP H H C O - - - - - 0 0 b-3 3333 3,5-DBP H H C O O Me O - - 0 1 b-3 3334 3,5-DBP H H C O O Me S - - 0 1 b-3 3335 tBu Ph Ph Si O O H O CH2CH2 O 1 1 b-3 3336 tBu Ph Ph Si O S H O CH2CH2 O 1 1 b-3 3337 tBu Ph Ph Si O - - - - - 0 0 b-3 3338 tBu Ph Ph Si O O Me O - - 0 1 b-3 3339 tBu Ph Ph Si O O Me S - - 0 1 b-3 3340 3,4-DBP H H C O O H O CH2CH2 O 1 1 c-2 3341 3,4-DBP H H C O S H O CH2CH2 O 1 1 c-2 3342 3,4-DBP H H C O - - - - - 0 0 c-2 3343 3,4-DBP H H C O O Me O - - 0 1 c-2 3344 3,4-DBP H H C O O Me S - - 0 1 c-2 3345 Ph Ph Ph C O O H O CH2CH2 O 1 1 c-2 3346 Ph Ph Ph C O S H O CH2CH2 O 1 1 c-2 3347 Ph Ph Ph C O - - - - - 0 0 c-2 3348 Ph Ph Ph C O O Me O - - 0 1 c-2 3349 Ph Ph Ph C O O Me S - - 0 1 c-2 3350 3,5-DBP H H C O O H O CH2CH2 O 1 1 c-2 3351 3,5-DBP H H C O S H O CH2CH2 O 1 1 c-2 3352 3,5-DBP H H C O - - - - - 0 0 c-2 3353 3,5-DBP H H C O O Me O - - 0 1 c-2 3354 3,5-DBP H H C O O Me S - - 0 1 c-2 3355 tBu Ph Ph Si O O H O CH2CH2 O 1 1 c-2 3356 tBu Ph Ph Si O S H O CH2CH2 O 1 1 c-2 3357 tBu Ph Ph Si O - - - - - 0 0 c-2 3358 tBu Ph Ph Si O O Me O - - 0 1 c-2 3359 tBu Ph Ph Si O O Me S - - 0 1 c-2 3360 3,4-DBP H H C O O H O CH2CH2 O 1 1 c-3 3361 3,4-DBP H H C O S H O CH2CH2 O 1 1 c-3 3362 3,4-DBP H H C O - - - - - 0 0 c-3 3363 3,4-DBP H H C O O Me O - - 0 1 c-3 3364 3,4-DBP H H C O O Me S - - 0 1 c-3 3365 Ph Ph Ph C O O H O CH2CH2 O 1 1 c-3 3366 Ph Ph Ph C O S H O CH2CH2 O 1 1 c-3 3367 Ph Ph Ph C O - - - - - 0 0 c-3 3368 Ph Ph Ph C O O Me O - - 0 1 c-3 3369 Ph Ph Ph C O O Me S - - 0 1 c-3 3370 3,5-DBP H H C O O H O CH2CH2 O 1 1 c-3 3371 3,5-DBP H H C O S H O CH2CH2 O 1 1 c-3 3372 3,5-DBP H H C O - - - - - 0 0 c-3 3373 3,5-DBP H H C O O Me O - - 0 1 c-3 3374 3,5-DBP H H C O O Me S - - 0 1 c-3 3375 tBu Ph Ph Si O O H O CH2CH2 O 1 1 c-3 3376 tBu Ph Ph Si O S H O CH2CH2 O 1 1 c-3 3377 tBu Ph Ph Si O - - - - - 0 0 c-3 3378 tBu Ph Ph Si O O Me O - - 0 1 c-3 3379 tBu Ph Ph Si O O Me S - - 0 1 c-3 3380 3,4-DBP H H C O O H O CH2CH2 O 1 1 d-2 3381 3,4-DBP H H C O S H O CH2CH2 O 1 1 d-2 3382 3,4-DBP H H C O - - - - - 0 0 d-2 3383 3,4-DBP H H C O O Me O - - 0 1 d-2 3384 3,4-DBP H H C O O Me S - - 0 1 d-2 3385 Ph Ph Ph C O O H O CH2CH2 O 1 1 d-2 3386 Ph Ph Ph C O S H O CH2CH2 O 1 1 d-2 3387 Ph Ph Ph C O - - - - - 0 0 d-2 3388 Ph Ph Ph C O O Me O - - 0 1 d-2 3389 Ph Ph Ph C O O Me S - - 0 1 d-2 3390 3,5-DBP H H C O O H O CH2CH2 O 1 1 d-2 3391 3,5-DBP H H C O S H O CH2CH2 O 1 1 d-2 3392 3,5-DBP H H C O - - - - - 0 0 d-2 3393 3,5-DBP H H C O O Me O - - 0 1 d-2 3394 3,5-DBP H H C O O Me S - - 0 1 d-2 3395 tBu Ph Ph Si O O H O CH2CH2 O 1 1 d-2 3396 tBu Ph Ph Si O S H O CH2CH2 O 1 1 d-2 3397 tBu Ph Ph Si O - - - - - 0 0 d-2 3398 tBu Ph Ph Si O O Me O - - 0 1 d-2 3399 tBu Ph Ph Si O O Me S - - 0 1 d-2 3400 3,4-DBP H H C O O H O CH2CH2 O 1 1 d-3 3401 3,4-DBP H H C O S H O CH2CH2 O 1 1 d-3 3402 3,4-DBP H H C O - - - - - 0 0 d-3 3403 3,4-DBP H H C O O Me O - - 0 1 d-3 3404 3,4-DBP H H C O O Me S - - 0 1 d-3 3405 Ph Ph Ph C O O H O CH2CH2 O 1 1 d-3 3406 Ph Ph Ph C O S H O CH2CH2 O 1 1 d-3 3407 Ph Ph Ph C O - - - - - 0 0 d-3 3408 Ph Ph Ph C O O Me O - - 0 1 d-3 3409 Ph Ph Ph C O O Me S - - 0 1 d-3 3410 3,5-DBP H H C O O H O CH2CH2 O 1 1 d-3 3411 3,5-DBP H H C O S H O CH2CH2 O 1 1 d-3 3412 3,5-DBP H H C O - - - - - 0 0 d-3 3413 3,5-DBP H H C O O Me O - - 0 1 d-3 3414 3,5-DBP H H C O O Me S - - 0 1 d-3 3415 tBu Ph Ph Si O O H O CH2CH2 O 1 1 d-3 3416 tBu Ph Ph Si O S H O CH2CH2 O 1 1 d-3 3417 tBu Ph Ph Si O - - - - - 0 0 d-3 3418 tBu Ph Ph Si O O Me O - - 0 1 d-3 3419 tBu Ph Ph Si O O Me S - - 0 1 d-3 ──────────────────────────────────── 上記例示化合物のうち、好適な化合物としては、１から
４４０まで、４５４、４７６、５８６、６９６、８０
６、９１６、１０２６、１１３６、１２４６、１３５
６、１４６６、１５７６、１６８６、１７６３、１７７
３、１７９３、１９７９、１９８０、１９９０から１９
９４まで、２２５０、２３２６から２９０６まで、２９
４０，２９４１，２９４２，２９６０，２９６１，２９
６２，３０００，３００１，３００２，３０２０，３０
２１，３０２２，３０６０，３０６１，３０６２，３０
８０，３０８１，３０８２，３１００，３１０１，３１
０２，３１２０，３１２１，３１２２，３１４０，３１
４１，３１４２，３１６０，３１６１，３１６２，３１
８０，３１８１，３１８２，３２００，３２０１，３２
０２，３２２０，３２２１，３２２２，３２４０，３２
４１，３２４２，３２６０，３２６１，３２６２，３２
８０，３２８１，３２８２，３３００，３３０１，３３
０２，３３２１，３３２２，３３２３，３３４０，３３
４１，３３４２，３３６０，３３６１，３３６２，３３
８０，３３８１，３３８２，３４００，３４０１，３４
０２の化合物をあげることができる。[Table 1] ──────────────────────────────────── Number R 1 R 2 R 3 ZY 1 Y 2 R Four Y 3 XY Four nm array ──────────────────────────────────── 1 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-1 2 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-1 3 3,4-DBP HHCO-----0 0 1-1 4 3,4-DBP HHCOO Me O--0 1 1-1 5 3,4-DBP HHCOO Me S-- 0 1 1-1 6 3,4-DBP HHCOO 2-ClPh O--0 1 1-1 7 3,4-DBP HHCO CH 2 HO--0 1 1-1 8 3,4-DBP HHCO CH 2 HS--0 1 1-1 9 3,4-DBP HHCO PhE HO--0 1 1-1 10 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 1-1 11 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 1-1 12 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 13 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-1 14 Ph Ph Ph CO-----0 0 1-1 15 Ph Ph Ph COO Me O--0 1 1-1 16 Ph Ph Ph COO Me S--0 1 1-1 17 Ph Ph Ph COO 2-ClPh O--0 1 1-1 18 Ph Ph Ph CO CH 2 HO--0 1 1-1 19 Ph Ph Ph CO CH 2 HS--0 1 1-1 20 Ph Ph Ph CO PhE HO--0 1 1-1 21 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 1-1 22 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 1-1 23 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-1 24 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-1 25 3,5-DBP HHCO-----0 0 1-1 26 3,5-DBP HHCOO Me O--0 1 1-1 27 3,5-DBP HHCOO Me S-- 0 1 1-1 28 3,5-DBP HHCOO 2-ClPh O--0 1 1-1 29 3,5-DBP HHCO CH 2 HO--0 1 1-1 30 3,5-DBP HHCO CH 2 HS--0 1 1-1 31 3,5-DBP HHCO PhE HO--0 1 1-1 32 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 1-1 33 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 1-1 34 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 1-1 35 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 1-1 36 4-MeOPh 4-MeOPh Ph CO-----0 0 1-1 37 4-MeOPh 4-MeOPh Ph COO Me O--0 1 1-1 38 4-MeOPh 4-MeOPh Ph COO Me S--0 1 1-1 39 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 1-1 40 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 1-1 41 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 1-1 42 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 1-1 43 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 1-1 44 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 1-1 45 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 46 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 1-1 47 4-MeOPh Ph Ph CO-----0 0 1-1 48 4-MeOPh Ph Ph COO Me O--0 1 1-1 49 4-MeOPh Ph Ph COO Me S-- 0 1 1-1 50 4-MeOPh Ph Ph COO 2-ClPh O--0 1 1-1 51 4-MeOPh Ph Ph CO CH 2 HO--0 1 1-1 52 4-MeOPh Ph Ph CO CH 2 HS--0 1 1-1 53 4-MeOPh Ph Ph CO PhE HO--0 1 1-1 54 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 1-1 55 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 1-1 56 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-1 57 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-1 58 tBu Ph Ph Si O-----0 0 1-1 59 tBu Ph Ph Si OO Me O--0 1 1-1 60 tBu Ph Ph Si OO Me S--0 1 1 -1 61 tBu Ph Ph Si OO 2-ClPh O--0 1 1-1 62 tBu Ph Ph Si O CH 2 HO--0 1 1-1 63 tBu Ph Ph Si O CH 2 HS--0 1 1-1 64 tBu Ph Ph Si O PhE HO--0 1 1-1 65 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 1-1 66 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 1-1 67 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 1-1 68 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 1-1 69 Ph Ph Ph CS-----0 0 1-1 70 Ph Ph Ph CSO Me O--0 1 1-1 71 Ph Ph Ph CSO Me S--0 1 1-1 72 Ph Ph Ph CSO 2-ClPh O--0 1 1-1 73 Ph Ph Ph CS CH 2 HO--0 1 1-1 74 Ph Ph Ph CS CH 2 HS--0 1 1-1 75 Ph Ph Ph CS PhE HO--0 1 1-1 76 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 1-1 77 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 1-1 78 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 1-1 79 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 1-1 80 4-BnOPh HHCO-----0 0 1-1 81 4-BnOPh HHCOO Me O--0 1 1-1 82 4-BnOPh HHCOO Me S--0 1 1-1 83 4-BnOPh HHCOO 2-ClPh O--0 1 1-1 84 4-BnOPh HHCO CH 2 HO--0 1 1-1 85 4-BnOPh HHCO CH 2 HS--0 1 1-1 86 4-BnOPh HHCO PhE HO--0 1 1-1 87 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 1-1 88 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 1-1 89 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 1-1 90 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 1-1 91 Ph Xanthen-9-yl O-----0 0 1-1 92 Ph Xanthen-9-yl OO Me O--0 1 1-1 93 Ph Xanthen-9-yl OO Me S--0 1 1-1 94 Ph Xanthen-9-yl OO 2-ClPh O--0 1 1-1 95 Ph Xanthen-9-yl O CH 2 HO--0 1 1-1 96 Ph Xanthen-9-yl O CH 2 HS--0 1 1-1 97 Ph Xanthen-9-yl O PhE HO--0 1 1-1 98 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 1-1 99 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 1-1 100 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 1-1 101 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 1-1 102 Ph Fluoren-9-yl O-----0 0 1-1 103 Ph Fluoren-9-yl OO Me O--0 1 1-1 104 Ph Fluoren-9-yl OO Me S--0 1 1-1 105 Ph Fluoren-9-yl OO 2-ClPh O--0 1 1-1 106 Ph Fluoren-9-yl O CH 2 HO--0 1 1-1 107 Ph Fluoren-9-yl O CH 2 HS--0 1 1-1 108 Ph Fluoren-9-yl O PhE HO--0 1 1-1 109 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 1-1 110 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 1-1 111 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 112 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 113 3,4-DBP HHCO-----0 0 114 3,4-DBP HHCOO Me O--0 1 115 3,4-DBP HHCOO Me S--0 1 116 3,4-DBP HHCOO 2-ClPh O--0 1 117 3,4-DBP HHCO CH 2 HO--0 1 118 3,4-DBP HHCO CH 2 HS--0 1 119 3,4-DBP HHCO PhE HO--0 1 120 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 121 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 122 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 123 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1 14 Ph Ph Ph CO-----0 0 125 Ph Ph Ph COO Me O--0 1 126 Ph Ph Ph COO Me S--0 1 127 Ph Ph Ph COO 2-ClPh O--0 1 128 Ph Ph Ph CO CH 2 HO--0 1 129 Ph Ph Ph CO CH 2 HS--0 1 130 Ph Ph Ph CO PhE HO--0 1 131 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 132 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 133 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 134 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 135 3,5-DBP HHCO-----0 0 136 3,5-DBP HHCOO Me O--0 1 137 3,5-DBP HHCOO Me S--0 1 138 3,5-DBP HHCOO 2-ClPh O--0 1 139 3,5-DBP HHCO CH 2 HO--0 1 140 3,5-DBP HHCO CH 2 HS--0 1 141 3,5-DBP HHCO PhE HO--0 1 142 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 143 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 144 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 145 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 146 4-MeOPh 4-MeOPh Ph CO-----0 0 147 4-MeOPh 4-MeOPh Ph COO Me O--0 1 148 4-MeOPh 4-MeOPh Ph COO Me S--0 1 149 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 150 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 151 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 152 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 153 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 154 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 155 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 156 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 157 4-MeOPh Ph Ph CO-----0 0 158 4-MeOPh Ph Ph COO Me O--0 1 159 4-MeOPh Ph Ph COO Me S--0 1 160 4-MeOPh Ph Ph COO 2-ClPh O--0 1 161 4-MeOPh Ph Ph CO CH 2 HO--0 1 162 4-MeOPh Ph Ph CO CH 2 HS--0 1 163 4-MeOPh Ph Ph CO PhE HO--0 1 164 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 165 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 166 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 167 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 168 tBu Ph Ph Si O-----0 0 169 tBu Ph Ph Si OO Me O--0 1 170 tBu Ph Ph Si OO Me S--0 1 171 tBu Ph Ph Si OO 2-ClPh O --0 1 172 tBu Ph Ph Si O CH 2 HO--0 1 173 tBu Ph Ph Si O CH 2 HS--0 1 174 tBu Ph Ph Si O PhE HO--0 1 175 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 176 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 177 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 178 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 179 Ph Ph Ph CS-----0 0 180 Ph Ph Ph CSO Me O--0 1 181 Ph Ph Ph CSO Me S--0 1 182 Ph Ph Ph CSO 2-ClPh O--0 1 183 Ph Ph Ph CS CH 2 HO--0 1 184 Ph Ph Ph CS CH 2 HS--0 1 185 Ph Ph Ph CS PhE HO--0 1 186 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 187 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 188 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 189 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 190 4-BnOPh HHCO-----0 0 191 4-BnOPh HHCOO Me O--0 1 192 4-BnOPh HHCOO Me S--0 1 193 4-BnOPh HHCOO 2-ClPh O--0 1 194 4-BnOPh HHCO CH 2 HO--0 1 195 4-BnOPh HHCO CH 2 HS--0 1 196 4-BnOPh HHCO PhE HO--0 1 197 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 198 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 199 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 200 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 201 Ph Xanthen-9-yl O-----0 0 202 Ph Xanthen-9-yl OO Me O--0 1 203 Ph Xanthen-9-yl OO Me S--0 1 204 Ph Xanthen- 9-yl OO 2-ClPh O--0 1 205 Ph Xanthen-9-yl O CH 2 HO--0 1 206 Ph Xanthen-9-yl O CH 2 HS--0 1 207 Ph Xanthen-9-yl O PhE HO--0 1 208 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 209 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 210 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 211 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 12 212 Ph Fluoren-9-yl O-----0 0 213 Ph Fluoren-9-yl OO Me O--0 1 214 Ph Fluoren-9-yl OO Me S--0 1 215 Ph Fluoren- 9-yl OO 2-ClPh O--0 1 216 Ph Fluoren-9-yl O CH 2 HO--0 1 217 Ph Fluoren-9-yl O CH 2 HS--0 1 218 Ph Fluoren-9-yl O PhE HO--0 1 219 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 220 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 221 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 3-1 222 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 3-1 223 3,4-DBP HHCO-----0 0 3-1 224 3,4-DBP HHCOO Me O--0 1 3-1 225 3,4-DBP HHCOO Me S-- 0 1 3-1 226 3,4-DBP HHCOO 2-ClPh O--0 1 3-1 227 3,4-DBP HHCO CH 2 HO--0 1 3-1 228 3,4-DBP HHCO CH 2 HS--0 1 3-1 229 3,4-DBP HHCO PhE HO--0 1 3-1 230 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 3-1 231 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 3-1 232 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 3-1 233 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 3-1 234 Ph Ph Ph CO-----0 0 3-1 235 Ph Ph Ph COO Me O--0 1 3-1 236 Ph Ph COO Me S--0 1 3-1 237 Ph Ph Ph COO 2-ClPh O--0 1 3-1 238 Ph Ph Ph CO CH 2 HO--0 1 3-1 239 Ph Ph Ph CO CH 2 HS--0 1 3-1 240 Ph Ph Ph CO PhE HO--0 1 3-1 241 Ph Ph Ph CO CO N Pr O CH 2 CH 2 O 1 1 3-1 242 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 3-1 243 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 3-1 244 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 3-1 245 3,5-DBP HHCO-----0 0 3-1 246 3,5-DBP HHCOO Me O--0 1 3-1 247 3,5-DBP HHCOO Me S-- 0 1 3-1 248 3,5-DBP HHCOO 2-ClPh O--0 1 3-1 249 3,5-DBP HHCO CH 2 HO--0 1 3-1 250 3,5-DBP HHCO CH 2 HS--0 1 3-1 251 3,5-DBP HHCO PhE HO--0 1 3-1 252 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 3-1 253 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 3-1 254 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 3-1 255 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 3-1 256 4-MeOPh 4-MeOPh Ph CO-----0 0 3-1 257 4-MeOPh 4-MeOPh Ph COO Me O--0 1 3-1 258 4-MeOPh 4-MeOPh Ph COO Me S--0 1 3-1 259 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 3-1 260 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 3-1 261 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 3-1 262 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 3-1 263 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 3-1 264 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 3-1 265 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 3-1 266 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 3-1 267 4-MeOPh Ph Ph CO-----0 0 3-1 268 4-MeOPh Ph Ph COO Me O--0 1 3-1 269 4-MeOPh Ph Ph COO Me S-- 0 1 3-1 270 4-MeOPh Ph Ph COO 2-ClPh O--0 1 3-1 271 4-MeOPh Ph Ph CO CH 2 HO--0 1 3-1 272 4-MeOPh Ph Ph CO CH 2 HS--0 1 3-1 273 4-MeOPh Ph Ph CO PhE HO--0 1 3-1 274 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 3-1 275 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 3-1 276 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 3-1 277 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 3-1 278 tBu Ph Ph Si O-----0 0 3-1 279 tBu Ph Ph Si OO Me O--0 1 3-1 280 tBu Ph Ph Si OO Me S--0 1 3 -1 281 tBu Ph Ph Si OO 2-ClPh O--0 1 3-1 282 tBu Ph Ph Si O CH 2 HO--0 1 3-1 283 tBu Ph Ph Si O CH 2 HS--0 1 3-1 284 tBu Ph Ph Si O PhE HO--0 1 3-1 285 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 3-1 286 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 3-1 287 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 3-1 288 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 3-1 289 Ph Ph Ph CS-----0 0 3-1 290 Ph Ph Ph CSO Me O--0 1 3-1 291 Ph Ph Ph CSO Me S--0 1 3-1 292 Ph Ph Ph CSO 2-ClPh O--0 1 3-1 293 Ph Ph Ph CS CH 2 HO--0 1 3-1 294 Ph Ph Ph CS CH 2 HS--0 1 3-1 295 Ph Ph Ph CS PhE HO--0 1 3-1 296 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 3-1 297 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 3-1 298 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 3-1 299 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 3-1 300 4-BnOPh HHCO-----0 0 3-1 301 4-BnOPh HHCOO Me O--0 1 3-1 302 4-BnOPh HHCOO Me S--0 1 3-1 303 4-BnOPh HHCOO 2-ClPh O--0 1 3-1 304 4-BnOPh HHCO CH 2 HO--0 1 3-1 305 4-BnOPh HHCO CH 2 HS--0 1 3-1 306 4-BnOPh HHCO PhE HO--0 1 3-1 307 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 3-1 308 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 3-1 309 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 3-1 310 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 3-1 311 Ph Xanthen-9-yl O-----0 0 3-1 312 Ph Xanthen-9-yl OO Me O--0 1 3-1 313 Ph Xanthen-9-yl OO Me S--0 1 3-1 314 Ph Xanthen-9-yl OO 2-ClPh O--0 1 3-1 315 Ph Xanthen-9-yl O CH 2 HO--0 1 3-1 316 Ph Xanthen-9-yl O CH 2 HS--0 1 3-1 317 Ph Xanthen-9-yl O PhE HO--0 1 3-1 318 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 3-1 319 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 3-1 320 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 3-1 321 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 3-1 322 Ph Fluoren-9-yl O-----0 0 3-1 323 Ph Fluoren-9-yl OO Me O--0 1 3-1 324 Ph Fluoren-9-yl OO Me S--0 1 3-1 325 Ph Fluoren-9-yl OO 2-ClPh O--0 1 3-1 326 Ph Fluoren-9-yl O CH 2 HO--0 1 3-1 327 Ph Fluoren-9-yl O CH 2 HS--0 1 3-1 328 Ph Fluoren-9-yl O PhE HO--0 1 3-1 329 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 3-1 330 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 3-1 331 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 332 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 333 3,4-DBP HHCO-----0 0 334 3,4-DBP HHCOO Me O--0 1 335 3,4-DBP HHCOO Me S--0 1 336 3,4-DBP HHCOO 2-ClPh O--0 1 337 3,4-DBP HHCO CH 2 HO--0 1 338 3,4-DBP HHCO CH 2 HS--0 1 339 3,4-DBP HHCO PhE HO--0 1 340 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 341 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 342 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 343 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 3 4 4 Ph Ph Ph CO-----0 0 345 Ph Ph Ph COO Me O--0 1 346 Ph Ph Ph COO Me S--0 1 347 Ph Ph Ph COO 2-ClPh O--0 1 348 Ph Ph Ph CO CH 2 HO--0 1 349 Ph Ph Ph CO CH 2 HS--0 1 350 Ph Ph Ph CO PhE HO--0 1 351 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 352 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 353 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 354 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 355 3,5-DBP HHCO-----0 0 356 3,5-DBP HHCOO Me O--0 1 357 3,5-DBP HHCOO Me S--0 1 358 3,5-DBP HHCOO 2-ClPh O--0 1 359 3,5-DBP HHCO CH 2 HO--0 1 360 3,5-DBP HHCO CH 2 HS--0 1 361 3,5-DBP HHCO PhE HO--0 1 362 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 363 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 364 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 365 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 366 4-MeOPh 4-MeOPh Ph CO-----0 0 367 4-MeOPh 4-MeOPh Ph COO Me O--0 1 368 4-MeOPh 4-MeOPh Ph COO Me S--0 1 369 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 370 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 371 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 372 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 373 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 374 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 375 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 376 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 377 4-MeOPh Ph Ph CO-----0 0 378 4-MeOPh Ph Ph COO Me O--0 1 379 4-MeOPh Ph Ph COO Me S--0 1 380 4-MeOPh Ph Ph COO 2-ClPh O--0 1 381 4-MeOPh Ph Ph CO CH 2 HO--0 1 382 4-MeOPh Ph Ph CO CH 2 HS--0 1 383 4-MeOPh Ph Ph CO PhE HO--0 1 384 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 385 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 386 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 387 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 388 tBu Ph Ph Si O-----0 0 389 tBu Ph Ph Si OO Me O--0 1 390 tBu Ph Ph Si OO Me S--0 1 391 tBu Ph Ph Si OO 2-ClPh O --0 1 392 tBu Ph Ph Si O CH 2 HO--0 1 393 tBu Ph Ph Si O CH 2 HS--0 1 394 tBu Ph Ph Si O PhE HO--0 1 395 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 396 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 397 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 398 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 399 Ph Ph Ph CS-----0 0 400 Ph Ph Ph CSO Me O--0 1 401 Ph Ph Ph CSO Me S--0 1 402 Ph Ph Ph CSO 2-ClPh O--0 1 403 Ph Ph Ph CS CH 2 HO--0 1 404 Ph Ph Ph CS CH 2 HS--0 1 405 Ph Ph Ph CS PhE HO--0 1 406 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 407 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 408 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 409 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 410 4-BnOPh HHCO-----0 0 411 4-BnOPh HHCOO Me O--0 1 412 4-BnOPh HHCOO Me S--0 1 413 4-BnOPh HHCOO 2-ClPh O--0 1 414 4-BnOPh HHCO CH 2 HO--0 1 415 4-BnOPh HHCO CH 2 HS--0 1 416 4-BnOPh HHCO PhE HO--0 1 417 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 418 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 419 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 420 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 421 Ph Xanthen-9-yl O-----0 0 422 Ph Xanthen-9-yl OO Me O--0 1 423 Ph Xanthen-9-yl OO Me S--0 1 424 Ph Xanthen- 9-yl OO 2-ClPh O--0 1 425 Ph Xanthen-9-yl O CH 2 HO--0 1 426 Ph Xanthen-9-yl O CH 2 HS--0 1 427 Ph Xanthen-9-yl O PhE HO--0 1 428 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 429 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 430 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 431 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 432 Ph Fluoren-9-yl O-----0 0 433 Ph Fluoren-9-yl OO Me O--0 1 434 Ph Fluoren-9-yl OO Me S--0 1 435 Ph Fluoren- 9-yl OO 2-ClPh O--0 1 436 Ph Fluoren-9-yl O CH 2 HO--0 1 437 Ph Fluoren-9-yl O CH 2 HS--0 1 438 Ph Fluoren-9-yl O PhE HO--0 1 439 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 440 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 441 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 442 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 443 3,4-DBP HHCO-----0 0 444 3,4-DBP HHCOO Me O--0 1 445 3,4-DBP HHCOO Me S--0 1 446 3,4-DBP HHCOO 2-ClPh O--0 1 447 3,4-DBP HHCO CH 2 HO--0 1 448 3,4-DBP HHCO CH 2 HS--0 1 449 3,4-DBP HHCO PhE HO--0 1 450 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 451 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 452 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 453 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 454 Ph Ph Ph CO-----0 0 455 Ph Ph Ph COO Me O--0 1 456 Ph Ph Ph COO Me S--0 1 457 Ph Ph Ph COO 2-ClPh O--0 1 458 Ph Ph Ph CO CH 2 HO--0 1 459 Ph Ph Ph CO CH 2 HS--0 1 460 Ph Ph Ph CO PhE HO--0 1 461 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 462 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 463 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 464 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 465 3,5-DBP HHCO-----0 0 466 3,5-DBP HHCOO Me O--0 1 467 3,5-DBP HHCOO Me S--0 1 468 3,5-DBP HHCOO 2-ClPh O--0 1 469 3,5-DBP HHCO CH 2 HO--0 1 470 3,5-DBP HHCO CH 2 HS--0 1 471 3,5-DBP HHCO PhE HO--0 1 472 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 473 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 474 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 475 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 476 4-MeOPh 4-MeOPh Ph CO-----0 0 477 4-MeOPh 4-MeOPh Ph COO Me O--0 1 478 4-MeOPh 4-MeOPh Ph COO Me S--0 1 479 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 480 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 481 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 482 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 483 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 484 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 485 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 486 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 487 4-MeOPh Ph Ph CO-----0 0 488 4-MeOPh Ph Ph COO Me O--0 1 489 4-MeOPh Ph Ph COO Me S--0 1 490 4-MeOPh Ph Ph COO 2-ClPh O--0 1 491 4-MeOPh Ph Ph CO CH 2 HO--0 1 492 4-MeOPh Ph Ph CO CH 2 HS--0 1 493 4-MeOPh Ph Ph CO PhE HO--0 1 494 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 495 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 496 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 497 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 498 tBu Ph Ph Si O-----0 0 499 tBu Ph Ph Si OO Me O--0 1 500 tBu Ph Ph Si OO Me S--0 1 501 tBu Ph Ph Si OO 2-ClPh O --0 1 502 tBu Ph Ph Si O CH 2 HO--0 1 503 tBu Ph Ph Si O CH 2 HS--0 1 504 tBu Ph Ph Si O PhE HO--0 1 505 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 506 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 507 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 508 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 50 9 Ph Ph Ph CS-----0 0 510 Ph Ph Ph CSO Me O--0 1 511 Ph Ph Ph CSO Me S--0 1 512 Ph Ph Ph CSO 2-ClPh O--0 1 513 Ph Ph Ph CS CH 2 HO--0 1 514 Ph Ph Ph CS CH 2 HS--0 1 515 Ph Ph Ph CS PhE HO--0 1 516 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 517 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 518 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 519 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 520 4-BnOPh HHCO-----0 0 521 4-BnOPh HHCOO Me O--0 1 522 4-BnOPh HHCOO Me S--0 1 523 4-BnOPh HHCOO 2-ClPh O--0 1 524 4-BnOPh HHCO CH 2 HO--0 1 525 4-BnOPh HHCO CH 2 HS--0 1 526 4-BnOPh HHCO PhE HO--0 1 527 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 528 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 529 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 530 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 531 Ph Xanthen-9-yl O-----0 0 532 Ph Xanthen-9-yl OO Me O--0 1 533 Ph Xanthen-9-yl OO Me S--0 1 534 Ph Xanthen- 9-yl OO 2-ClPh O--0 1 535 Ph Xanthen-9-yl O CH 2 HO--0 1 536 Ph Xanthen-9-yl O CH 2 HS--0 1 537 Ph Xanthen-9-yl O PhE HO--0 1 538 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 539 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 540 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 541 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 542 Ph Fluoren-9-yl O-----0 0 543 Ph Fluoren-9-yl OO Me O--0 1 544 Ph Fluoren-9-yl OO Me S--0 1 545 Ph Fluoren- 9-yl OO 2-ClPh O--0 1 546 Ph Fluoren-9-yl O CH 2 HO--0 1 547 Ph Fluoren-9-yl O CH 2 HS--0 1 548 Ph Fluoren-9-yl O PhE HO--0 1 549 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 550 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 551 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 552 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 553 3,4-DBP HHCO-----0 0 554 3,4-DBP HHCOO Me O--0 1 555 3,4-DBP HHCOO Me S--0 1 556 3,4-DBP HHCOO 2-ClPh O--0 1 557 3,4-DBP HHCO CH 2 HO--0 1 558 3,4-DBP HHCO CH 2 HS--0 1 559 3,4-DBP HHCO PhE HO--0 1 560 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 561 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 562 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 563 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 564 Ph Ph Ph CO-----0 0 565 Ph Ph Ph COO Me O--0 1 566 Ph Ph Ph COO Me S--0 1 567 Ph Ph Ph COO 2-ClPh O--0 1 568 Ph Ph Ph CO CH 2 HO--0 1 569 Ph Ph Ph CO CH 2 HS--0 1 570 Ph Ph Ph CO PhE HO--0 1 571 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 572 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 573 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 574 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 575 3,5-DBP HHCO-----0 0 576 3,5-DBP HHCOO Me O--0 1 577 3,5-DBP HHCOO Me S--0 1 578 3,5-DBP HHCOO 2-ClPh O--0 1 579 3,5-DBP HHCO CH 2 HO--0 1 580 3,5-DBP HHCO CH 2 HS--0 1 581 3,5-DBP HHCO PhE HO--0 1 582 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 583 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 584 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 585 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 586 4-MeOPh 4-MeOPh Ph CO-----0 0 587 4-MeOPh 4-MeOPh Ph COO Me O--0 1 588 4-MeOPh 4-MeOPh Ph COO Me S--0 1 589 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 590 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 591 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 592 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 593 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 594 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 595 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 596 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 597 4-MeOPh Ph Ph CO-----0 0 598 4-MeOPh Ph Ph COO Me O--0 1 599 4-MeOPh Ph Ph COO Me S--0 1 600 4-MeOPh Ph Ph COO 2-ClPh O--0 1 601 4-MeOPh Ph Ph CO CH 2 HO--0 1 602 4-MeOPh Ph Ph CO CH 2 HS--0 1 603 4-MeOPh Ph Ph CO PhE HO--0 1 604 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 605 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 606 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 607 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 608 tBu Ph Ph Si O-----0 0 609 tBu Ph Ph Si OO Me O--0 1 610 tBu Ph Ph Si OO Me S--0 1 611 tBu Ph Ph Si OO 2-ClPh O --0 1 612 tBu Ph Ph Si O CH 2 HO--0 1 613 tBu Ph Ph Si O CH 2 HS--0 1 614 tBu Ph Ph Si O PhE HO--0 1 615 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 616 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 617 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 618 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 619 Ph Ph Ph CS-----0 0 620 Ph Ph Ph CSO Me O--0 1 621 Ph Ph Ph CSO Me S--0 1 622 Ph Ph Ph CSO 2-ClPh O--0 1 623 Ph Ph Ph CS CH 2 HO--0 1 624 Ph Ph Ph CS CH 2 HS--0 1 625 Ph Ph Ph CS PhE HO--0 1 626 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 627 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 628 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 629 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 630 4-BnOPh HHCO-----0 0 631 4-BnOPh HHCOO Me O--0 1 632 4-BnOPh HHCOO Me S--0 1 633 4-BnOPh HHCOO 2-ClPh O--0 1 634 4-BnOPh HHCO CH 2 HO--0 1 635 4-BnOPh HHCO CH 2 HS--0 1 636 4-BnOPh HHCO PhE HO--0 1 637 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 638 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 639 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 640 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 641 Ph Xanthen-9-yl O-----0 0 642 Ph Xanthen-9-yl OO Me O--0 1 643 Ph Xanthen-9-yl OO Me S--0 1 644 Ph Xanthen- 9-yl OO 2-ClPh O--0 1 645 Ph Xanthen-9-yl O CH 2 HO--0 1 646 Ph Xanthen-9-yl O CH 2 HS--0 1 647 Ph Xanthen-9-yl O PhE HO--0 1 648 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 649 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 650 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 651 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 653 Ph Fluoren-9-yl OO Me O--0 1 654 Ph Fluoren-9-yl OO Me S--0 1 655 Ph Fluoren-9-yl OO 2-ClPh O--0 1 656 Ph Fluoren -9-yl O CH 2 HO--0 1 657 Ph Fluoren-9-yl O CH 2 HS--0 1 658 Ph Fluoren-9-yl O PhE HO--0 1 659 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 660 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 661 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 662 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 663 3,4-DBP HHCO-----0 0 664 3,4-DBP HHCOO Me O--0 1 665 3,4-DBP HHCOO Me S--0 1 666 3,4-DBP HHCOO 2-ClPh O--0 1 667 3,4-DBP HHCO CH 2 HO--0 1 668 3,4-DBP HHCO CH 2 HS--0 1 669 3,4-DBP HHCO PhE HO--0 1 670 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 671 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 672 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 673 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 674 Ph Ph Ph CO-----0 0 675 Ph Ph Ph COO Me O--0 1 676 Ph Ph Ph COO Me S--0 1 677 Ph Ph Ph COO 2-ClPh O--0 1 678 Ph Ph Ph CO CH 2 HO--0 1 679 Ph Ph Ph CO CH 2 HS--0 1 680 Ph Ph Ph CO PhE HO--0 1 681 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 682 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 683 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 684 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 685 3,5-DBP HHCO-----0 0 686 3,5-DBP HHCOO Me O--0 1 687 3,5-DBP HHCOO Me S--0 1 688 3,5-DBP HHCOO 2-ClPh O--0 1 689 3,5-DBP HHCO CH 2 HO--0 1 690 3,5-DBP HHCO CH 2 HS--0 1 691 3,5-DBP HHCO PhE HO--0 1 692 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 693 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 694 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 695 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 696 4-MeOPh 4-MeOPh Ph CO-----0 0 697 4-MeOPh 4-MeOPh Ph COO Me O--0 1 698 4-MeOPh 4-MeOPh Ph COO Me S--0 1 699 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 700 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 701 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 702 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 703 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 704 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 705 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 706 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 707 4-MeOPh Ph Ph CO-----0 0 708 4-MeOPh Ph Ph COO Me O--0 1 709 4-MeOPh Ph Ph COO Me S--0 1 711 4-MeOPh Ph Ph CO CH 2 HO--0 1 712 4-MeOPh Ph Ph CO CH 2 HS--0 1 713 4-MeOPh Ph Ph CO PhE HO--0 1 714 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 715 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 716 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 717 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 718 tBu Ph Ph Si O-----0 0 719 tBu Ph Ph Si OO Me O--0 1 720 tBu Ph Ph Si OO Me S--0 1 721 tBu Ph Ph Si OO 2-ClPh O --0 1 722 tBu Ph Ph Si O CH 2 HO--0 1 723 tBu Ph Ph Si O CH 2 HS--0 1 724 tBu Ph Ph Si O PhE HO--0 1 725 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 726 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 727 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 728 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 729 Ph Ph Ph CS-----0 0 730 Ph Ph Ph CSO Me O--0 1 731 Ph Ph Ph CSO Me S--0 1 732 Ph Ph Ph CSO 2-ClPh O--0 1 733 Ph Ph Ph CS CH 2 HO--0 1 734 Ph Ph Ph CS CH 2 HS--0 1 735 Ph Ph Ph CS PhE HO--0 1 736 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 737 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 738 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 739 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 740 4-BnOPh HHCO-----0 0 741 4-BnOPh HHCOO Me O--0 1 742 4-BnOPh HHCOO Me S--0 1 743 4-BnOPh HHCOO 2-ClPh O--0 1 744 4-BnOPh HHCO CH 2 HO--0 1 745 4-BnOPh HHCO CH 2 HS--0 1 746 4-BnOPh HHCO PhE HO--0 1 747 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 748 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 749 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 750 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 751 Ph Xanthen-9-yl O-----0 0 752 Ph Xanthen-9-yl OO Me O--0 1 753 Ph Xanthen-9-yl OO Me S--0 1 754 Ph Xanthen- 9-yl OO 2-ClPh O--0 1 755 Ph Xanthen-9-yl O CH 2 HO--0 1 756 Ph Xanthen-9-yl O CH 2 HS--0 1 757 Ph Xanthen-9-yl O PhE HO--0 1 758 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 759 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 760 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 761 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 762 Ph Fluoren-9-yl O-----0 0 763 Ph Fluoren-9-yl OO Me O--0 1 764 Ph Fluoren-9-yl OO Me S--0 1 765 Ph Fluoren- 9-yl OO 2-ClPh O--0 1 766 Ph Fluoren-9-yl O CH 2 HO--0 1 767 Ph Fluoren-9-yl O CH 2 HS--0 1 768 Ph Fluoren-9-yl O PhE HO--0 1 769 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 770 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 771 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 772 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 773 3,4-DBP HHCO-----0 0 774 3,4-DBP HHCOO Me O--0 1 775 3,4-DBP HHCOO Me S--0 1 776 3,4-DBP HHCOO 2-ClPh O--0 1 777 3,4-DBP HHCO CH 2 HO--0 1 778 3,4-DBP HHCO CH 2 HS--0 1 779 3,4-DBP HHCO PhE HO--0 1 780 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 781 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 782 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 783 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 784 Ph Ph Ph CO-----0 0 785 Ph Ph Ph COO Me O--0 1 786 Ph Ph Ph COO Me S--0 1 787 Ph Ph Ph COO 2-ClPh O--0 1 788 Ph Ph Ph CO CH 2 HO--0 1 789 Ph Ph Ph CO CH 2 HS--0 1 790 Ph Ph Ph CO PhE HO--0 1 791 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 792 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 793 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 794 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 795 3,5-DBP HHCO-----0 0 796 3,5-DBP HHCOO Me O--0 1 797 3,5-DBP HHCOO Me S--0 1 798 3,5-DBP HHCOO 2-ClPh O--0 1 799 3,5-DBP HHCO CH 2 HO--0 1 800 3,5-DBP HHCO CH 2 HS--0 1 801 3,5-DBP HHCO PhE HO--0 1 802 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 803 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 804 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 805 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 806 4-MeOPh 4-MeOPh Ph CO-----0 0 807 4-MeOPh 4-MeOPh Ph COO Me O--0 1 808 4-MeOPh 4-MeOPh Ph COO Me S--0 1 809 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 810 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 811 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 812 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 813 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 814 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 815 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 816 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 817 4-MeOPh Ph Ph CO-----0 0 818 4-MeOPh Ph Ph COO Me O--0 1 819 4-MeOPh Ph Ph COO Me S--0 1 820 4-MeOPh Ph Ph COO 2-ClPh O--0 1 821 4-MeOPh Ph Ph CO CH 2 HO--0 1 822 4-MeOPh Ph Ph CO CH 2 HS--0 1 823 4-MeOPh Ph Ph CO PhE HO--0 1 824 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 825 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 826 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 827 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 828 tBu Ph Ph Si O-----0 0 829 tBu Ph Ph Si OO Me O--0 1 830 tBu Ph Ph Si OO Me S--0 1 831 tBu Ph Ph Si OO 2-ClPh O --0 1 832 tBu Ph Ph Si O CH 2 HO--0 1 833 tBu Ph Ph Si O CH 2 HS--0 1 834 tBu Ph Ph Si O PhE HO--0 1 835 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 836 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 837 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 838 Ph Ph Ph CSSHO CH 2 CH 2 O 1 839 Ph Ph Ph CS-----0 0 840 Ph Ph Ph CSO Me O--0 1 841 Ph Ph Ph CSO Me S--0 1 842 Ph Ph Ph CSO 2-ClPh O--0 1 843 Ph Ph Ph CS CH 2 HO--0 1 844 Ph Ph Ph CS CH 2 HS--0 1 845 Ph Ph Ph CS PhE HO--0 1 846 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 847 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 848 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 849 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 850 4-BnOPh HHCO-----0 0 851 4-BnOPh HHCOO Me O--0 1 852 4-BnOPh HHCOO Me S--0 1 853 4-BnOPh HHCOO 2-ClPh O--0 1 854 4-BnOPh HHCO CH 2 HO--0 1 855 4-BnOPh HHCO CH 2 HS--0 1 856 4-BnOPh HHCO PhE HO--0 1 857 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 858 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 859 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 860 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 861 Ph Xanthen-9-yl O-----0 0 862 Ph Xanthen-9-yl OO Me O--0 1 863 Ph Xanthen-9-yl OO Me S--0 1 864 Ph Xanthen- 9-yl OO 2-ClPh O--0 1 865 Ph Xanthen-9-yl O CH 2 HO--0 1 866 Ph Xanthen-9-yl O CH 2 HS--0 1 867 Ph Xanthen-9-yl O PhE HO--0 1 868 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 869 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 870 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 871 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 872 Ph Fluoren-9-yl O-----0 0 873 Ph Fluoren-9-yl OO Me O--0 1 874 Ph Fluoren-9-yl OO Me S--0 1 875 Ph Fluoren- 9-yl OO 2-ClPh O--0 1 876 Ph Fluoren-9-yl O CH 2 HO--0 1 877 Ph Fluoren-9-yl O CH 2 HS--0 1 878 Ph Fluoren-9-yl O PhE HO--0 1 879 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 880 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 881 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 882 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 883 3,4-DBP HHCO-----0 0 884 3,4-DBP HHCOO Me O--0 1 885 3,4-DBP HHCOO Me S--0 1 886 3,4-DBP HHCOO 2-ClPh O--0 1 887 3,4-DBP HHCO CH 2 HO--0 1 888 3,4-DBP HHCO CH 2 HS--0 1 889 3,4-DBP HHCO PhE HO--0 1 890 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 891 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 892 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 893 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 894 Ph Ph Ph CO-----0 0 895 Ph Ph Ph COO Me O--0 1 896 Ph Ph Ph COO Me S--0 1 897 Ph Ph Ph COO 2-ClPh O--0 1 898 Ph Ph Ph CO CH 2 HO--0 1 899 Ph Ph Ph CO CH 2 HS--0 1 900 Ph Ph Ph CO PhE HO--0 1 901 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 902 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 903 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 904 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 905 3,5-DBP HHCO-----0 0 906 3,5-DBP HHCOO Me O--0 1 907 3,5-DBP HHCOO Me S--0 1 908 3,5-DBP HHCOO 2-ClPh O--0 1 909 3,5-DBP HHCO CH 2 HO--0 1 910 3,5-DBP HHCO CH 2 HS--0 1 911 3,5-DBP HHCO PhE HO--0 1 912 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 913 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 914 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 915 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 916 4-MeOPh 4-MeOPh Ph CO-----0 0 917 4-MeOPh 4-MeOPh Ph COO Me O--0 1 918 4-MeOPh 4-MeOPh Ph COO Me S--0 1 919 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 920 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 921 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 922 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 923 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 924 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 925 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 926 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 927 4-MeOPh Ph Ph CO-----0 0 928 4-MeOPh Ph Ph COO Me O--0 1 929 4-MeOPh Ph Ph COO Me S--0 1 930 4-MeOPh Ph Ph COO 2-ClPh O--0 1 931 4-MeOPh Ph Ph CO CH 2 HO--0 1 932 4-MeOPh Ph Ph CO CH 2 HS--0 1 933 4-MeOPh Ph Ph CO PhE HO--0 1 934 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 935 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 936 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 937 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 938 tBu Ph Ph Si O-----0 0 939 tBu Ph Ph Si OO Me O--0 1 940 tBu Ph Ph Si OO Me S--0 1 941 tBu Ph Ph Si OO 2-ClPh O --0 1 942 tBu Ph Ph Si O CH 2 HO--0 1 943 tBu Ph Ph Si O CH 2 HS--0 1 944 tBu Ph Ph Si O PhE HO--0 1 945 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 946 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 947 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 948 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 949 Ph Ph Ph CS-----0 0 950 Ph Ph Ph CSO Me O--0 1 951 Ph Ph Ph CSO Me S--0 1 952 Ph Ph Ph CSO 2-ClPh O--0 1 953 Ph Ph Ph CS CH 2 HO--0 1 954 Ph Ph Ph CS CH 2 HS--0 1 955 Ph Ph Ph CS PhE HO--0 1 956 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 957 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 958 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 959 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 960 4-BnOPh HHCO-----0 0 961 4-BnOPh HHCOO Me O--0 1 962 4-BnOPh HHCOO Me S--0 1 963 4-BnOPh HHCOO 2-ClPh O--0 1 964 4-BnOPh HHCO CH 2 HO--0 1 965 4-BnOPh HHCO CH 2 HS--0 1 966 4-BnOPh HHCO PhE HO--0 1 967 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 968 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 969 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 970 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 971 Ph Xanthen-9-yl O-----0 0 972 Ph Xanthen-9-yl OO Me O--0 1 973 Ph Xanthen-9-yl OO Me S--0 1 974 Ph Xanthen- 9-yl OO 2-ClPh O--0 1 975 Ph Xanthen-9-yl O CH 2 HO--0 1 976 Ph Xanthen-9-yl O CH 2 HS--0 1 977 Ph Xanthen-9-yl O PhE HO--0 1 978 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 979 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 980 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 981 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 982 Ph Fluoren-9-yl O-----0 0 983 Ph Fluoren-9-yl OO Me O--0 1 984 Ph Fluoren-9-yl OO Me S--0 1 985 Ph Fluoren- 9-yl OO 2-ClPh O--0 1 986 Ph Fluoren-9-yl O CH 2 HO--0 1 987 Ph Fluoren-9-yl O CH 2 HS--0 1 988 Ph Fluoren-9-yl O PhE HO--0 1 989 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 990 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 991 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 a 992 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 a 993 3,4-DBP HHCO-----0 0 a 994 3,4-DBP HHCOO Me O--0 1 a 995 3,4-DBP HHCOO Me S--0 1 a 996 3, 4-DBP HHCOO 2-ClPh O--0 1 Y 997 3,4-DBP HHCO CH 2 HO--0 1 a 998 3,4-DBP HHCO CH 2 HS--0 1 a 999 3,4-DBP HHCO PhE HO--0 1 a 1000 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 a 1001 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 a 1002 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 a 1003 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Y 1004 Ph Ph Ph CO-----0 0 Y 1005 Ph Ph Ph COO Me O--0 1 Y 1006 Ph Ph Ph COO Me S--0 1 Y 1007 Ph Ph Ph COO 2-ClPh O --0 1 a 1008 Ph Ph Ph CO CH 2 HO--0 1 a 1009 Ph Ph Ph CO CH 2 HS--0 1 a 1010 Ph Ph Ph CO PhE HO--0 1 a 1011 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 a 1012 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 a 1013 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 a 1014 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 a 1015 3,5-DBP HHCO-----0 0 a 1016 3,5-DBP HHCOO Me O--0 1 a 1017 3,5-DBP HHCOO Me S--0 1 a 1018 3, 5-DBP HHCOO 2-ClPh O--0 1 Y 1019 3,5-DBP HHCO CH 2 HO--0 1 a 1020 3,5-DBP HHCO CH 2 HS--0 1 a 1021 3,5-DBP HHCO PhE HO--0 1 a 1022 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 a 1023 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 b 1024 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 a 1025 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 a 1026 4-MeOPh 4-MeOPh Ph CO-----0 0 a 1027 4-MeOPh 4-MeOPh Ph COO Me O--0 1 a 1028 4-MeOPh 4-MeOPh Ph COO Me S-- 0 1 a 1029 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 a 1030 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 a 1031 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 a 1032 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 a 1033 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 a 1034 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 a 1035 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 a 1036 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 a 1037 4-MeOPh Ph Ph CO-----0 0 a 1038 4-MeOPh Ph Ph COO Me O--0 1 a 1039 4-MeOPh Ph Ph COO Me S--0 1 a 1040 4- MeOPh Ph Ph COO 2-ClPh O--0 1 a 1041 4-MeOPh Ph Ph CO CH 2 HO--0 1 a 1042 4-MeOPh Ph Ph CO CH 2 HS--0 1 a 1043 4-MeOPh Ph Ph CO PhE HO--0 1 a 1044 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 a 1045 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 a 1046 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 a 1047 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 a 1048 tBu Ph Ph Si O-----0 0 a 1049 tBu Ph Ph Si OO Me O--0 1 a 1050 tBu Ph Ph Si OO Me S--0 1 a 1051 tBu Ph Ph Si OO 2-ClPh O--0 1 a 1052 tBu Ph Ph Si O CH 2 HO--0 1 a 1053 tBu Ph Ph Si O CH 2 HS--0 1 a 1054 tBu Ph Ph Si O PhE HO--0 1 a 1055 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 a 1056 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 b 1057 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 a 1058 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 a 1059 Ph Ph Ph CS-----0 0 a 1060 Ph Ph Ph CSO Me O--0 1 a 1061 Ph Ph Ph CSO Me S--0 1 a 1062 Ph Ph Ph CSO 2-ClPh O --0 1 b 1063 Ph Ph Ph CS CH 2 HO--0 1 a 1064 Ph Ph Ph CS CH 2 HS--0 1 a 1065 Ph Ph Ph CS PhE HO--0 1 a 1066 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 a 1067 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 b 1068 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 a 1069 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 Y 1070 4-BnOPh HHCO-----0 0 Y 1071 4-BnOPh HHCOO Me O--0 1 Y 1072 4-BnOPh HHCOO Me S--0 1 Y 1073 4-BnOPh HHCOO 2-ClPh O --0 1 A 1074 4-BnOPh HHCO CH 2 HO--0 1 a 1075 4-BnOPh HHCO CH 2 HS--0 1 a 1076 4-BnOPh HHCO PhE HO--0 1 a 1077 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 a 1078 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 Lee 1079 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 A 1080 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 b 1081 Ph Xanthen-9-yl O-----0 0 b 1082 Ph Xanthen-9-yl OO Me O--0 1 b 1083 Ph Xanthen-9-yl OO Me S--0 1 b 1084 Ph Xanthen-9-yl OO 2-ClPh O--0 1 y 1085 Ph Xanthen-9-yl O CH 2 HO--0 1 I 1086 Ph Xanthen-9-yl O CH 2 HS--0 1 a 1087 Ph Xanthen-9-yl O PhE HO--0 1 a 1088 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 I 1089 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 a 1090 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 I 1091 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 b 1092 Ph Fluoren-9-yl O-----0 0 b 1093 Ph Fluoren-9-yl OO Me O--0 1 b 1094 Ph Fluoren-9-yl OO Me S--0 1 b 1095 Ph Fluoren-9-yl OO 2-ClPh O--0 1 Y 1096 Ph Fluoren-9-yl O CH 2 HO--0 1 I 1097 Ph Fluoren-9-yl O CH 2 HS--0 1 a 1098 Ph Fluoren-9-yl O PhE HO--0 1 a 1099 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 I 1100 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 b 1101 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 b 1102 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 b 1103 3,4-DBP HHCO-----0 0 b 1104 3,4-DBP HHCOO Me O--0 1 b 1105 3,4-DBP HHCOO Me S--0 1 b 1 106 3, 4-DBP HHCOO 2-ClPh O--0 1 Lo 1107 3,4-DBP HHCO CH 2 HO--0 1 RO 1108 3,4-DBP HHCO CH 2 HS--0 1 b 1109 3,4-DBP HHCO PhE HO--0 1 b 1110 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 b 1111 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 b 1112 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Ro 1113 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 b 1114 Ph Ph Ph CO-----0 0 b 1115 Ph Ph Ph COO Me O--0 1 b 1116 Ph Ph Ph COO Me S--0 1 b 1117 Ph Ph Ph COO 2-ClPh O --0 1 Ro 1118 Ph Ph Ph CO CH 2 HO--0 1 Ro 1119 Ph Ph Ph CO CH 2 HS--0 1 b 1120 Ph Ph Ph CO PhE HO--0 1 b 1121 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 Ro 1122 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 b 1123 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 b 1124 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 b 1125 3,5-DBP HHCO-----0 0 b 1126 3,5-DBP HHCOO Me O--0 1 b 1 127 3,5-DBP HHCOO Me S--0 1 b 1 128 3, 5-DBP HHCOO 2-ClPh O--0 1 Lo 1129 3,5-DBP HHCO CH 2 HO--0 1 RO 1130 3,5-DBP HHCO CH 2 HS--0 1 b 1131 3,5-DBP HHCO PhE HO--0 1 b 1132 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 Lo 1133 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 b 1134 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 b 1135 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 b 1136 4-MeOPh 4-MeOPh Ph CO-----0 0 b 1137 4-MeOPh 4-MeOPh Ph COO Me O--0 1 b 1138 4-MeOPh 4-MeOPh Ph COO Me S-- 0 1 b 1139 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 b 1140 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 b 1141 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 b 1142 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 b 1143 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 Lo 1144 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 b 1145 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 Lo 1146 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 b 1147 4-MeOPh Ph Ph CO-----0 0 b 1148 4-MeOPh Ph Ph COO Me O--0 1 b 1149 4-MeOPh Ph Ph COO Me S--0 1 b 1150 4- MeOPh Ph Ph COO 2-ClPh O--0 1 Lo 1151 4-MeOPh Ph Ph CO CH 2 HO--0 1 Lo 1152 4-MeOPh Ph Ph CO CH 2 HS--0 1 b 1153 4-MeOPh Ph Ph CO PhE HO--0 1 b 1154 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 Lo 1155 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 b 1156 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 b 1157 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 b 1158 tBu Ph Ph Si O-----0 0 b 1159 tBu Ph Ph Si OO Me O--0 1 b 1160 tBu Ph Ph Si OO Me S--0 1 b 1161 tBu Ph Ph Si OO 2-ClPh O--0 1 b 1162 tBu Ph Ph Si O CH 2 HO--0 1 b 1163 tBu Ph Ph Si O CH 2 HS--0 1 b 1164 tBu Ph Ph Si O PhE HO--0 1 b 1165 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 R 1166 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 b 1167 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 Ro 1168 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 b 1169 Ph Ph Ph CS-----0 0 b 1170 Ph Ph Ph CSO Me O--0 1 b 1171 Ph Ph Ph CSO Me S--0 1 b 1172 Ph Ph Ph CSO 2-ClPh O --0 1 b 1173 Ph Ph Ph CS CH 2 HO--0 1 RO 1174 Ph Ph Ph CS CH 2 HS--0 1 b 1175 Ph Ph Ph CS PhE HO--0 1 b 1176 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 Ro 1177 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 b 1178 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 b 1179 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 b 1180 4-BnOPh HHCO-----0 0 b 1181 4-BnOPh HHCOO Me O--0 1 b 1182 4-BnOPh HHCOO Me S--0 1 b 1183 4-BnOPh HHCOO 2-ClPh O --0 1 b 1184 4-BnOPh HHCO CH 2 HO--0 1 b 1185 4-BnOPh HHCO CH 2 HS--0 1 b 1186 4-BnOPh HHCO PhE HO--0 1 b 1187 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 Ro 1188 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 Ro 1189 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 Ro 1190 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 b 1191 Ph Xanthen-9-yl O-----0 0 b 1192 Ph Xanthen-9-yl OO Me O--0 1 b 1193 Ph Xanthen-9-yl OO Me S--0 1 b 1194 Ph Xanthen-9-yl OO 2-ClPh O--0 1 Lo 1195 Ph Xanthen-9-yl O CH 2 HO--0 1 Ro 1196 Ph Xanthen-9-yl O CH 2 HS--0 1 b 1197 Ph Xanthen-9-yl O PhE HO--0 1 b 1198 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 Ro 1199 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 B 1200 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 B 1201 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 b 1202 Ph Fluoren-9-yl O-----0 0 b 1203 Ph Fluoren-9-yl OO Me O--0 1 b 1204 Ph Fluoren-9-yl OO Me S--0 1 b 1205 Ph Fluoren-9-yl OO 2-ClPh O--0 1 R 1206 Ph Fluoren-9-yl O CH 2 HO--0 1 RO 1207 Ph Fluoren-9-yl O CH 2 HS--0 1 b 1208 Ph Fluoren-9-yl O PhE HO--0 1 b 1209 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 B 1210 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 b 1211 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 Ha 12 12 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Ha 1213 3,4-DBP HHCO-----0 0 Ha 1214 3,4-DBP HHCOO Me O--0 1 Ha 1215 3,4-DBP HHCOO Me S--0 1 Ha 1216 3, 4-DBP HHCOO 2-ClPh O--0 1 Ha 1217 3,4-DBP HHCO CH 2 HO--0 1 Ha 1218 3,4-DBP HHCO CH 2 HS--0 1 Ha 1219 3,4-DBP HHCO PhE HO--0 1 Ha 1220 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 Ha 1221 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 Ha 1222 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Ha 1223 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Ha 1224 Ph Ph Ph CO-----0 0 Ha 1225 Ph Ph Ph COO Me O--0 1 Ha 1226 Ph Ph Ph COO Me S--0 1 Ha 1227 Ph Ph Ph COO 2-ClPh O --0 1 Ha 1228 Ph Ph Ph CO CH 2 HO--0 1 Ha 1229 Ph Ph Ph CO CH 2 HS--0 1 Ha 1230 Ph Ph Ph CO PhE HO--0 1 Ha 1231 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 Ha 1232 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 Ha 1233 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Ha 1234 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Ha 1235 3,5-DBP HHCO-----0 0 Ha 1236 3,5-DBP HHCOO Me O--0 1 Ha 1237 3,5-DBP HHCOO Me S--0 1 Ha 1238 3, 5-DBP HHCOO 2-ClPh O--0 1 Ha 1239 3,5-DBP HHCO CH 2 HO--0 1 Ha 1240 3,5-DBP HHCO CH 2 HS--0 1 Ha 1241 3,5-DBP HHCO PhE HO--0 1 Ha 1242 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 Ha 1243 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 Ha 1244 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 Ha 1245 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 Ha 1246 4-MeOPh 4-MeOPh Ph CO-----0 0 Ha 1247 4-MeOPh 4-MeOPh Ph COO Me O--0 1 Ha 1248 4-MeOPh 4-MeOPh Ph COO Me S-- 0 1 Ha 1249 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 Ha 1250 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 Ha 1251 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 Ha 1252 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 Ha 1253 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 Ha 1254 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 Ha 1255 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 Ha 1256 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 Ha 1257 4-MeOPh Ph Ph CO-----0 0 Ha 1258 4-MeOPh Ph Ph COO Me O--0 1 Ha 1259 4-MeOPh Ph Ph COO Me S--0 1 Ha 1260 4- MeOPh Ph Ph COO 2-ClPh O--0 1 Ha 1261 4-MeOPh Ph Ph CO CH 2 HO--0 1 Ha 1262 4-MeOPh Ph Ph CO CH 2 HS--0 1 Ha 1263 4-MeOPh Ph Ph CO PhE HO--0 1 Ha 1264 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 Ha 1265 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 Ha 1266 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 Ha 1267 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 Ha 1268 tBu Ph Ph Si O-----0 0 Ha 1269 tBu Ph Ph Si OO Me O--0 1 Ha 1270 tBu Ph Ph Si OO Me S--0 1 Ha 1271 tBu Ph Ph Si OO 2-ClPh O--0 1 Ha 1272 tBu Ph Ph Si O CH 2 HO--0 1 Ha 1273 tBu Ph Ph Si O CH 2 HS--0 1 Ha 1274 tBu Ph Ph Si O PhE HO--0 1 Ha 1275 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 Ha 1276 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 Ha 1277 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 Ha 1278 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 Ha 1279 Ph Ph Ph CS-----0 0 Ha 1280 Ph Ph Ph CSO Me O--0 1 Ha 1281 Ph Ph Ph CSO Me S--0 1 Ha 1282 Ph Ph Ph CSO 2-ClPh O --0 1 Ha 1283 Ph Ph Ph CS CH 2 HO--0 1 Ha 1284 Ph Ph Ph CS CH 2 HS--0 1 Ha 1285 Ph Ph Ph CS PhE HO--0 1 Ha 1286 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 Ha 1287 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 Ha 1288 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 Ha 1289 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 Ha 1290 4-BnOPh HHCO-----0 0 Ha 1291 4-BnOPh HHCOO Me O--0 1 Ha 1292 4-BnOPh HHCOO Me S--0 1 Ha 1293 4-BnOPh HHCOO 2-ClPh O --0 1 Ha 1294 4-BnOPh HHCO CH 2 HO--0 1 Ha 1295 4-BnOPh HHCO CH 2 HS--0 1 Ha 1296 4-BnOPh HHCO PhE HO--0 1 Ha 1297 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 Ha 1298 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 Ha 1299 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 Ha 1300 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 Ha 1301 Ph Xanthen-9-yl O-----0 0 Ha 1302 Ph Xanthen-9-yl OO Me O--0 1 Ha 1303 Ph Xanthen-9-yl OO Me S--0 1 Ha 1304 Ph Xanthen-9-yl OO 2-ClPh O--0 1 Ha 1305 Ph Xanthen-9-yl O CH 2 HO--0 1 Ha 1306 Ph Xanthen-9-yl O CH 2 HS--0 1 Ha 1307 Ph Xanthen-9-yl O PhE HO--0 1 Ha 1308 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 Ha 1309 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 Ha 1310 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 Ha 1311 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 Ha 1312 Ph Fluoren-9-yl O-----0 0 Ha 1313 Ph Fluoren-9-yl OO Me O--0 1 Ha 1314 Ph Fluoren-9-yl OO Me S--0 1 Ha 1315 Ph Fluoren-9-yl OO 2-ClPh O--0 1 Ha 1316 Ph Fluoren-9-yl O CH 2 HO--0 1 Ha 1317 Ph Fluoren-9-yl O CH 2 HS--0 1 Ha 1318 Ph Fluoren-9-yl O PhE HO--0 1 Ha 1319 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 Ha 1320 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 Ha 1321 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 D 1322 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Ni 1323 3,4-DBP HHCO-----0 0 Ni 1324 3,4-DBP HHCOO Me O--0 1 Ni 1325 3,4-DBP HHCOO Me S--0 1 Ni 1326 3, 4-DBP HHCOO 2-ClPh O--0 1 D 1327 3,4-DBP HHCO CH 2 HO--0 1 D 1328 3,4-DBP HHCO CH 2 HS--0 1 Ni 1329 3,4-DBP HHCO PhE HO--0 1 Ni 1330 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 D 1331 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 2 1332 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Ni 1333 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Ni 1334 Ph Ph Ph CO-----0 0 Ni 1335 Ph Ph Ph COO Me O--0 1 Ni 1336 Ph Ph Ph COO Me S--0 1 Ni 1337 Ph Ph Ph COO 2-ClPh O --0 1 D 1338 Ph Ph Ph CO CH 2 HO--0 1 D 1339 Ph Ph Ph CO CH 2 HS--0 1 Ni 1340 Ph Ph Ph CO PhE HO--0 1 Ni 1341 Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 D 1342 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 2 1343 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 D 1344 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Ni 1345 3,5-DBP HHCO-----0 0 Ni 1346 3,5-DBP HHCOO Me O--0 1 Ni 1347 3,5-DBP HHCOO Me S--0 1 Ni 1349 3, 5-DBP HHCO CH 2 HO--0 1 D 1350 3,5-DBP HHCO CH 2 HS--0 1 Ni 1351 3,5-DBP HHCO PhE HO--0 1 Ni 1352 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 2 1353 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 D 1354 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 2 1355 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 Ni 1356 4-MeOPh 4-MeOPh Ph CO------0 0 Ni 1357 4-MeOPh 4-MeOPh Ph COO Me O--0 1 Ni 1358 4-MeOPh 4-MeOPh Ph COO Me S-- 0 1 Ni 1359 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 Ni 1360 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 D 1361 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 Ni 1362 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 Ni 1363 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 D 1364 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 2 1365 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 2 1366 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 Ni 1367 4-MeOPh Ph Ph CO-----0 0 Ni 1368 4-MeOPh Ph Ph COO Me O--0 1 Ni 1369 4-MeOPh Ph Ph COO Me S--0 1 Ni 1370 4- MeOPh Ph Ph COO 2-ClPh O--0 1 D 1371 4-MeOPh Ph Ph CO CH 2 HO--0 1 D 1372 4-MeOPh Ph Ph CO CH 2 HS--0 1 Ni 1373 4-MeOPh Ph Ph CO PhE HO--0 1 Ni 1374 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 2 1375 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 2 1376 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 2 1377 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 Ni 1378 tBu Ph Ph Si O-----0 0 Ni 1379 tBu Ph Ph Si OO Me O--0 1 Ni 1380 tBu Ph Ph Si OO Me S--0 1 Ni 1381 tBu Ph Ph Si OO 2-ClPh O--0 1 D 1382 tBu Ph Ph Si O CH 2 HO--0 1 Ni 1383 tBu Ph Ph Si O CH 2 HS--0 1 Ni 1384 tBu Ph Ph Si O PhE HO--0 1 Ni 1385 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 2 1386 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 2 1387 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 2 1388 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 Ni 1389 Ph Ph Ph CS-----0 0 Ni 1390 Ph Ph Ph CSO Me O--0 1 Ni 1391 Ph Ph Ph CSO Me S--0 1 Ni 1392 Ph Ph Ph CSO 2-ClPh O --0 1 D 1393 Ph Ph Ph CS CH 2 HO--0 1 D 1394 Ph Ph Ph CS CH 2 HS--0 1 Ni 1395 Ph Ph Ph CS PhE HO--0 1 Ni 1396 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 2 1397 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 2 1398 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 2 1399 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 Ni 1400 4-BnOPh HHCO-----0 0 Ni 1401 4-BnOPh HHCOO Me O--0 1 Ni 1402 4-BnOPh HHCOO Me S--0 1 Ni 1403 4-BnOPh HHCOO 2-ClPh O --0 1 D 1404 4-BnOPh HHCO CH 2 HO--0 1 D 1405 4-BnOPh HHCO CH 2 HS--0 1 Ni 1406 4-BnOPh HHCO PhE HO--0 1 Ni 1407 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 2 1408 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 2 1409 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 2 1410 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 Ni 1411 Ph Xanthen-9-yl O-----0 0 Ni 1412 Ph Xanthen-9-yl OO Me O--0 1 Ni 1413 Ph Xanthen-9-yl OO Me S--0 1 Ni 1414 Ph Xanthen-9-yl OO 2-ClPh O--0 1 D 1415 Ph Xanthen-9-yl O CH 2 HO--0 1 Ni 1416 Ph Xanthen-9-yl O CH 2 HS--0 1 Ni 1417 Ph Xanthen-9-yl O PhE HO--0 1 Ni 1418 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 2 1419 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 D 1420 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 D 1421 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 D 1422 Ph Fluoren-9-yl O-----0 0 D 1423 Ph Fluoren-9-yl OO Me O--0 1 D 1424 Ph Fluoren-9-yl OO Me S--0 1 D 1425 Ph Fluoren-9-yl OO 2-ClPh O--0 1 D 1426 Ph Fluoren-9-yl O CH 2 HO--0 1 2 1427 Ph Fluoren-9-yl O CH 2 HS--0 1 Ni 1428 Ph Fluoren-9-yl O PhE HO--0 1 Ni 1429 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 2 1430 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 D 1431 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 Ho 1432 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Ho 1433 3,4-DBP HHCO-----0 0 Ho 1434 3,4-DBP HHCOO Me O--0 1 Ho 1435 3,4-DBP HHCOO Me S--0 1 Ho 1436 3, 4-DBP HHCOO 2-ClPh O--0 1 ho 1437 3,4-DBP HHCO CH 2 HO--0 1 ho 1438 3,4-DBP HHCO CH 2 HS--0 1 Ho 1439 3,4-DBP HHCO PhE HO--0 1 Ho 1440 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 Ho 1441 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 Ho 1442 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Ho 1443 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Ho 1444 Ph Ph Ph CO-----0 0 Ho 1445 Ph Ph Ph COO Me O--0 1 Ho 1446 Ph Ph Ph COO Me S--0 1 Ho 1447 Ph Ph Ph COO 2-ClPh O --0 1 Ho 1448 Ph Ph Ph CO CH 2 HO--0 1 Ho 1449 Ph Ph Ph CO CH 2 HS--0 1 Ho 1450 Ph Ph Ph CO PhE HO--0 1 Ho 1451 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 Ho 1452 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 Ho 1453 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Ho 1454 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Ho 1455 3,5-DBP HHCO-----0 0 Ho 1456 3,5-DBP HHCOO Me O--0 1 Ho 1457 3,5-DBP HHCOO Me S--0 1 Ho 1458 3, 5-DBP HHCOO 2-ClPh O--0 1 Ho 1459 3,5-DBP HHCO CH 2 HO--0 1 Ho 1460 3,5-DBP HHCO CH 2 HS--0 1 Ho 1461 3,5-DBP HHCO PhE HO--0 1 Ho 1462 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 Ho 1463 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 Ho 1464 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 Ho 1465 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 Ho 1466 4-MeOPh 4-MeOPh Ph CO-----0 0 Ho 1467 4-MeOPh 4-MeOPh Ph COO Me O--0 1 Ho 1468 4-MeOPh 4-MeOPh Ph COO Me S-- 0 1 Ho 1469 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 Ho 1470 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 Ho 1471 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 E 1472 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 E 1473 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 Ho 1474 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 Ho 1475 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 Ho 1476 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 Ho 1477 4-MeOPh Ph Ph CO-----0 0 Ho 1478 4-MeOPh Ph Ph COO Me O--0 1 Ho 1479 4-MeOPh Ph Ph COO Me S--0 1 Ho 1480 4- MeOPh Ph Ph COO 2-ClPh O--0 1 Ho 1481 4-MeOPh Ph Ph CO CH 2 HO--0 1 Ho 1482 4-MeOPh Ph Ph CO CH 2 HS--0 1 Ho 1483 4-MeOPh Ph Ph CO PhE HO--0 1 Ho 1484 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 Ho 1485 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 Ho 1486 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 Ho 1487 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 Ho 1488 tBu Ph Ph Si O-----0 0 Ho 1489 tBu Ph Ph Si OO Me O--0 1 Ho 1490 tBu Ph Ph Si OO Me S--0 1 Ho 1491 tBu Ph Ph Si OO 2-ClPh O--0 1 Ho 1492 tBu Ph Ph Si O CH 2 HO--0 1 Ho 1493 tBu Ph Ph Si O CH 2 HS--0 1 Ho 1494 tBu Ph Ph Si O PhE HO--0 1 Ho 1495 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 Ho 1496 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 Ho 1497 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 Ho 1498 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 Ho 1499 Ph Ph Ph CS-----0 0 Ho 1500 Ph Ph Ph CSO Me O--0 1 Ho 1501 Ph Ph Ph CSO Me S--0 1 Ho 1502 Ph Ph Ph CSO 2-ClPh O --0 1 Ho 1503 Ph Ph Ph CS CH 2 HO--0 1 Ho 1504 Ph Ph Ph CS CH 2 HS--0 1 Ho 1505 Ph Ph Ph CS PhE HO--0 1 Ho 1506 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 Ho 1507 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 Ho 1508 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 Ho 1509 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 Ho 1510 4-BnOPh HHCO-----0 0 Ho 1511 4-BnOPh HHCOO Me O--0 1 Ho 1512 4-BnOPh HHCOO Me S--0 1 Ho 1513 4-BnOPh HHCOO 2-ClPh O --0 1 Ho 1514 4-BnOPh HHCO CH 2 HO--0 1 Ho 1515 4-BnOPh HHCO CH 2 HS--0 1 E 1516 4-BnOPh HHCO PhE HO--0 1 E 1517 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 Ho 1518 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 Ho 1519 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 Ho 1520 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 Ho 1521 Ph Xanthen-9-yl O-----0 0 Ho 1522 Ph Xanthen-9-yl OO Me O--0 1 Ho 1523 Ph Xanthen-9-yl OO Me S--0 1 Ho 1524 Ph Xanthen-9-yl OO 2-ClPh O--0 1 Ho 1525 Ph Xanthen-9-yl O CH 2 HO--0 1 Ho 1526 Ph Xanthen-9-yl O CH 2 HS--0 1 Ho 1527 Ph Xanthen-9-yl O PhE HO--0 1 Ho 1528 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 Ho 1529 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 Ho 1530 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 Ho 1531 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 E 1532 Ph Fluoren-9-yl O-----0 0 E 1533 Ph Fluoren-9-yl OO Me O--0 1 E 1534 Ph Fluoren-9-yl OO Me S--0 1 E 1535 Ph Fluoren-9-yl OO 2-ClPh O--0 1 Ho 1536 Ph Fluoren-9-yl O CH 2 HO--0 1 Ho 1537 Ph Fluoren-9-yl O CH 2 HS--0 1 E 1538 Ph Fluoren-9-yl O PhE HO--0 1 E 1539 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 Ho 1540 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 Ho 1541 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 F 1542 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 F 1543 3,4-DBP HHCO-----0 0 F 1544 3,4-DBP HHCOO Me O--0 1 F 1545 3,4-DBP HHCOO Me S--0 1 F 1546 3, 4-DBP HHCOO 2-ClPh O--0 1 F 1547 3,4-DBP HHCO CH 2 HO--0 1 F 1548 3,4-DBP HHCO CH 2 HS--0 1 f 1549 3,4-DBP HHCO PhE HO--0 1 f 1550 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 F 1551 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 F 1552 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 F 1553 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 F 1554 Ph Ph Ph CO-----0 0 F 1555 Ph Ph Ph COO Me O--0 1 F 1556 Ph Ph Ph COO Me S--0 1 F 1557 Ph Ph Ph COO 2-ClPh O --0 1 F 1558 Ph Ph Ph CO CH 2 HO--0 1 F 1559 Ph Ph Ph CO CH 2 HS--0 1 f 1560 Ph Ph Ph CO PhE HO--0 1 f 1561 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 F 1562 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 F 1563 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 F 1564 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 F 1565 3,5-DBP HHCO-----0 0 F 1566 3,5-DBP HHCOO Me O--0 1 F 1567 3,5-DBP HHCOO Me S--0 1 F 1568 3, 5-DBP HHCOO 2-ClPh O--0 1 F 1569 3,5-DBP HHCO CH 2 HO--0 1 F 1570 3,5-DBP HHCO CH 2 HS--0 1 f 1571 3,5-DBP HHCO PhE HO--0 1 f 1572 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 F 1573 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 F 1574 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 F 1575 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 F 1576 4-MeOPh 4-MeOPh Ph CO-----0 0 F 1577 4-MeOPh 4-MeOPh Ph COO Me O--0 1 F 1578 4-MeOPh 4-MeOPh Ph COO Me S-- 0 1 F 1579 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 F 1580 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 F 1581 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 f 1582 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 f 1583 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 F 1584 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 F 1585 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 F 1586 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 F 1587 4-MeOPh Ph Ph CO-----0 0 F 1588 4-MeOPh Ph Ph COO Me O--0 1 F 1589 4-MeOPh Ph Ph COO Me S--0 1 F 1590 4- MeOPh Ph Ph COO 2-ClPh O--0 1 F 1591 4-MeOPh Ph Ph CO CH 2 HO--0 1 F 1592 4-MeOPh Ph Ph CO CH 2 HS--0 1 f 1593 4-MeOPh Ph Ph CO PhE HO--0 1 f 1594 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 F 1595 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 F 1596 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 F 1597 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 F 1598 tBu Ph Ph Si O-----0 0 F 1599 tBu Ph Ph Si OO Me O--0 1 F 1600 tBu Ph Ph Si OO Me S--0 1 F 1601 tBu Ph Ph Si OO 2-ClPh O--0 1 F 1602 tBu Ph Ph Si O CH 2 HO--0 1 F 1603 tBu Ph Ph Si O CH 2 HS--0 1 f 1604 tBu Ph Ph Si O PhE HO--0 1 f 1605 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 F 1606 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 F 1607 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 F 1608 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 F 1609 Ph Ph Ph CS-----0 0 F 1610 Ph Ph Ph CSO Me O--0 1 F 1611 Ph Ph Ph CSO Me S--0 1 F 1612 Ph Ph Ph CSO 2-ClPh O --0 1 F 1613 Ph Ph Ph CS CH 2 HO--0 1 F 1614 Ph Ph Ph CS CH 2 HS--0 1 f 1615 Ph Ph Ph CS PhE HO--0 1 f 1616 Ph Ph Ph CS CS NH Pr O CH 2 CH 2 O 1 1 F 1617 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 F 1618 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 F 1619 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 F 1620 4-BnOPh HHCO-----0 0 F 1621 4-BnOPh HHCOO Me O--0 1 F 1622 4-BnOPh HHCOO Me S--0 1 F 1623 4-BnOPh HHCOO 2-ClPh O --0 1 F 1624 4-BnOPh HHCO CH 2 HO--0 1 F 1625 4-BnOPh HHCO CH 2 HS--0 1 F 1626 4-BnOPh HHCO PhE HO--0 1 F 1627 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 F 1628 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 F 1629 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 F 1630 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 F 1631 Ph Xanthen-9-yl O-----0 0 F 1632 Ph Xanthen-9-yl OO Me O--0 1 F 1633 Ph Xanthen-9-yl OO Me S--0 1 F 1634 Ph Xanthen-9-yl OO 2-ClPh O--0 1 F 1635 Ph Xanthen-9-yl O CH 2 HO--0 1 F 1636 Ph Xanthen-9-yl O CH 2 HS--0 1 F 1637 Ph Xanthen-9-yl O PhE HO--0 1 F 1638 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 F 1639 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 F 1640 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 F 1641 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 F 1642 Ph Fluoren-9-yl O-----0 0 F 1643 Ph Fluoren-9-yl OO Me O--0 1 F 1644 Ph Fluoren-9-yl OO Me S--0 1 F 1645 Ph Fluoren-9-yl OO 2-ClPh O--0 1 F 1646 Ph Fluoren-9-yl O CH 2 HO--0 1 F 1647 Ph Fluoren-9-yl O CH 2 HS--0 1 F 1648 Ph Fluoren-9-yl O PhE HO--0 1 F 1649 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 F 1650 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 F 1651 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1652 3,4-DBP HHCOSHO CH 2 CH 2 O 1 to 1653 3,4-DBP HHCO-----0 0 to 1654 3,4-DBP HHCOO Me O--0 1 to 1655 3,4-DBP HHCOO Me S--0 1 to 1656 3, 4-DBP HHCOO 2-ClPh O--0 1 to 1657 3,4-DBP HHCO CH 2 HO--0 1 TO 1658 3,4-DBP HHCO CH 2 HS--0 1 to 1659 3,4-DBP HHCO PhE HO--0 1 to 1660 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 To 1661 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 To 1662 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 To 1663 Ph Ph Ph COSHO CH 2 CH 2 O 1 to 16 64 Ph Ph Ph CO-----0 0 to 1665 Ph Ph Ph COO Me O--0 1 to 1666 Ph Ph Ph COO Me S--0 1 to 1668 Ph Ph Ph CO CH 2 HO--0 1 TO 1669 Ph Ph Ph CO CH 2 HS--0 1 to 1670 Ph Ph Ph CO PhE HO--0 1 to 1671 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 To 1672 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 to 1673 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1674 3,5-DBP HHCOSHO CH 2 CH 2 O 1 to 1675 3,5-DBP HHCO-----0 0 to 1676 3,5-DBP HHCOO Me O--0 1 to 1677 3,5-DBP HHCOO Me S--0 1 to 1678 3, 5-DBP HHCOO 2-ClPh O--0 1 TO 1679 3,5-DBP HHCO CH 2 HO--0 1 TO 1680 3,5-DBP HHCO CH 2 HS--0 1 to 1681 3,5-DBP HHCO PhE HO--0 1 to 1682 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 to 1683 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 to 1684 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 To 1685 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 to 1686 4-MeOPh 4-MeOPh Ph CO-----0 0 to 1687 4-MeOPh 4-MeOPh Ph COO Me O--0 1 to 1688 4-MeOPh 4-MeOPh Ph COO Me S-- 0 1 to 1689 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 to 1690 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 TO 1691 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 to 1692 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 to 1693 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 to 1694 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 to 1695 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 To 1696 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 to 1697 4-MeOPh Ph Ph CO-----0 0 to 1698 4-MeOPh Ph Ph COO Me O--0 1 to 1699 4-MeOPh Ph Ph COO Me S--0 1 to 1700 4- MeOPh Ph Ph COO 2-ClPh O--0 1 to 1701 4-MeOPh Ph Ph CO CH 2 HO--0 1 TO 1702 4-MeOPh Ph Ph CO CH 2 HS--0 1 to 1703 4-MeOPh Ph Ph CO PhE HO--0 1 to 1704 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 to 1705 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 to 1706 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 to 1707 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 to 1708 tBu Ph Ph Si O-----0 0 to 1709 tBu Ph Ph Si OO Me O--0 1 to 1710 tBu Ph Ph Si OO Me S--0 1 to 1711 tBu Ph Ph Si OO 2-ClPh O--0 1 TO 1712 tBu Ph Ph Si O CH 2 HO--0 1 TO 1713 tBu Ph Ph Si O CH 2 HS--0 1 to 1714 tBu Ph Ph Si O PhE HO--0 1 to 1715 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 11 1 1716 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 to 1717 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 7 17 Ph Ph Ph CSSHO CH 2 CH 2 O 1 to 17 19 Ph Ph Ph CS-----0 0 to 1720 Ph Ph Ph CSO Me O--0 1 to 1721 Ph Ph Ph CSO Me S--0 1 to 1722 Ph Ph Ph CSO 2-ClPh O --0 1 to 1723 Ph Ph Ph CS CH 2 HO--0 1 to 1724 Ph Ph Ph CS CH 2 HS--0 1 to 1725 Ph Ph Ph CS PhE HO--0 1 to 1726 Ph Ph Ph CS CS NH Pr O CH 2 CH 2 O 1 1 To 1727 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 to 1728 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 To 1729 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 to 1730 4-BnOPh HHCO-----0 0 to 1731 4-BnOPh HHCOO Me O--0 1 to 1732 4-BnOPh HHCOO Me S--0 1 to 1733 4-BnOPh HHCOO 2-ClPh O --0 1 TO 1734 4-BnOPh HHCO CH 2 HO--0 1 TO 1735 4-BnOPh HHCO CH 2 HS--0 1 to 1736 4-BnOPh HHCO PhE HO--0 1 to 1737 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 to 1738 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 to 1739 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 to 1740 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 To 1741 Ph Xanthen-9-yl O-----0 0 To 1742 Ph Xanthen-9-yl OO Me O--0 1 To 1743 Ph Xanthen-9-yl OO Me S--0 1 To 1744 Ph Xanthen-9-yl OO 2-ClPh O--0 1 To 1745 Ph Xanthen-9-yl O CH 2 HO--0 1 TO 1746 Ph Xanthen-9-yl O CH 2 HS--0 1 to 1747 Ph Xanthen-9-yl O PhE HO--0 1 to 1748 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 to 1749 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 to 1750 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 11 1 1751 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 To 1752 Ph Fluoren-9-yl O-----0 0 To 1753 Ph Fluoren-9-yl OO Me O--0 1 To 1754 Ph Fluoren-9-yl OO Me S--0 1 To 1755 Ph Fluoren-9-yl OO 2-ClPh O--0 1 To 1756 Ph Fluoren-9-yl O CH 2 HO--0 1 TO 1757 Ph Fluoren-9-yl O CH 2 HS--0 1 to 1758 Ph Fluoren-9-yl O PhE HO--0 1 to 1759 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 to 1760 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 to 1761 1-PYR HHCOOHO CH 2 CH 2 O 1 1 1-1 1762 1-PYR HHCOSHO CH 2 CH 2 O 1 1 1-1 1763 1-PYR HHCO-----0 0 1-1 1764 1-PYR HHCOO Me O--0 1 1-1 1765 1-PYR HHCOO Me S--0 1 1-1 1766 2-NAP HHCOOHO CH 2 CH 2 O 1 1 1-1 1767 2-NAP HHCOSHO CH 2 CH 2 O 1 1 1-1 1768 2-NAP HHCO-----0 0 1-1 1769 2-NAP HHCOO Me O--0 1 1-1 1770 2-NAP HHCOO Me S--0 1 1-1 1771 Ph Ph HCOOHO CH 2 CH 2 O 1 1 1-1 1772 Ph Ph HCOSHO CH 2 CH 2 O 1 1 1-1 1773 Ph Ph HCO-----0 0 1-1 1774 Ph Ph HCOO Me O--0 1 1-1 1775 Ph Ph HCOO Me S--0 1 1-1 1776 4-PhPh HHCOOHO CH 2 CH 2 O 1 1 1-1 1777 4-PhPh HHCOSHO CH 2 CH 2 O 1 1 1-1 1778 4-PhPh HHCO-----0 0 1-1 1779 4-PhPh HHCOO Me O--0 1 1-1 1780 4-PhPh HHCOO Me S--0 1 1-1 1781 2-PhPh HHCOOHO CH 2 CH 2 O 1 1 1-1 1782 2-PhPh HHCOSHO CH 2 CH 2 O 1 1 1-1 1783 2-PhPh HHCO-----0 0 1-1 1784 2-PhPh HHCOO Me O--0 1 1-1 1785 2-PhPh HHCOO Me S--0 1 1-1 1786 Ph Ph HCSOHO CH 2 CH 2 O 1 1 1-1 1787 Ph Ph HCSSHO CH 2 CH 2 O 1 1 1-1 1788 Ph Ph HCS-----0 0 1-1 1789 Ph Ph HCSO Me O--0 1 1-1 1790 Ph Ph HCSO Me S--0 1 1-1 1791 Ph Ph Ph C NH OHO CH 2 CH 2 O 1 1 1-1 1792 Ph Ph Ph C NH SHO CH 2 CH 2 O 1 1 1-1 1793 Ph Ph Ph C NH-----0 0 1-1 1794 Ph Ph Ph C NH O Me O--0 1 1-1 1795 Ph Ph Ph C NH O Me S--0 1 1-1 1796 1-PYR HHCOOHO CH 2 CH 2 O 1 1 1797 1-PYR HHCOSHO CH 2 CH 2 O 1 1 1798 1-PYR HHCO-----0 0 1799 1-PYR HHCOO Me O--0 1 1800 1-PYR HHCOO Me S--0 1 1801 2-NAP HHCOOHO CH 2 CH 2 O 1 1 1802 2-NAP HHCOSHO CH 2 CH 2 O 1 1 1803 2-NAP HHCO-----0 0 1804 2-NAP HHCOO Me O--0 1 1805 2-NAP HHCOO Me S--0 1 1806 Ph Ph HCOOHO CH 2 CH 2 O 1 1 1807 Ph Ph HCOSHO CH 2 CH 2 O 1 1 1808 Ph Ph HCO-----0 0 1809 Ph Ph HCOO Me O--0 1 1810 Ph Ph HCOO Me S--0 1 1811 4-PhPh HHCOOHO CH 2 CH 2 O 1 1 1812 4-PhPh HHCOSHO CH 2 CH 2 O 1 1 1813 4-PhPh HHCO-----0 0 1814 4-PhPh HHCOO Me O--0 1 1815 4-PhPh HHCOO Me S--0 1 1816 2-PhPh HHCOOHO CH 2 CH 2 O 1 1 1817 2-PhPh HHCOSHO CH 2 CH 2 O 1 1 1818 2-PhPh HHCO-----0 0 1819 2-PhPh HHCOO Me O--0 1 1820 2-PhPh HHCOO Me S--0 1 1821 Ph Ph HCSOHO CH 2 CH 2 O 1 1 1822 Ph Ph HCSSHO CH 2 CH 2 O 1 1 1823 Ph Ph HCS-----0 0 1824 Ph Ph HCSO Me O--0 1 1825 Ph Ph HCSO Me S--0 1 1826 Ph Ph Ph C NH OHO CH 2 CH 2 O 1 1 1827 Ph Ph Ph C NH SHO CH 2 CH 2 O 1 1 828 Ph Ph Ph C NH-----0 0 1829 Ph Ph Ph C NH O Me O--0 1 1830 Ph Ph Ph C NH O Me S--0 1 1831 1-PYR HHCOOHO CH 2 CH 2 O 1 1 3-1 1832 1-PYR HHCOSHO CH 2 CH 2 O 1 1 3-1 1833 1-PYR HHCO-----0 0 3-1 1834 1-PYR HHCOO Me O--0 1 3-1 1835 1-PYR HHCOO Me S--0 1 3-1 1836 2-NAP HHCOOHO CH 2 CH 2 O 1 1 3-1 1837 2-NAP HHCOSHO CH 2 CH 2 O 1 1 3-1 1838 2-NAP HHCO-----0 0 3-1 1839 2-NAP HHCOO Me O--0 1 3-1 1840 2-NAP HHCOO Me S--0 1 3-1 1841 Ph Ph HCOOHO CH 2 CH 2 O 1 1 3-1 1842 Ph Ph HCOSHO CH 2 CH 2 O 1 1 3-1 1843 Ph Ph HCO-----0 0 3-1 1844 Ph Ph HCOO Me O--0 1 3-1 1845 Ph Ph HCOO Me S--0 1 3-1 1846 4-PhPh HHCOOHO CH 2 CH 2 O 1 1 3-1 1847 4-PhPh HHCOSHO CH 2 CH 2 O 1 1 3-1 1848 4-PhPh HHCO-----0 0 3-1 1849 4-PhPh HHCOO Me O--0 1 3-1 1850 4-PhPh HHCOO Me S--0 1 3-1 1851 2-PhPh HHCOOHO CH 2 CH 2 O 1 1 3-1 1852 2-PhPh HHCOSHO CH 2 CH 2 O 1 1 3-1 1853 2-PhPh HHCO-----0 0 3-1 1854 2-PhPh HHCOO Me O--0 1 3-1 1855 2-PhPh HHCOO Me S--0 1 3-1 1856 Ph Ph HCSOHO CH 2 CH 2 O 1 1 3-1 1857 Ph Ph HCSSHO CH 2 CH 2 O 1 1 3-1 1858 Ph Ph HCS-----0 0 3-1 1859 Ph Ph HCSO Me O--0 1 3-1 1860 Ph Ph HCSO Me S--0 1 3-1 1861 Ph Ph Ph C NH OHO CH 2 CH 2 O 1 1 3-1 1862 Ph Ph Ph C NH SHO CH 2 CH 2 O 1 1 3-1 1863 Ph Ph Ph C NH-----0 0 3-1 1864 Ph Ph Ph C NH O Me O--0 1 3-1 1865 Ph Ph Ph C NH O Me S--0 1 3-1 1866 1-PYR HHCOOHO CH 2 CH 2 O 1 1 1867 1-PYR HHCOSHO CH 2 CH 2 O 1 1 1868 1-PYR HHCO-----0 0 1869 1-PYR HHCOO Me O--0 1 1870 1-PYR HHCOO Me S--0 1 1871 2-NAP HHCOOHO CH 2 CH 2 O 1 1 1872 2-NAP HHCOSHO CH 2 CH 2 O 1 1 1873 2-NAP HHCO-----0 0 1874 2-NAP HHCOO Me O--0 1 1875 2-NAP HHCOO Me S--0 1 1876 Ph Ph HCOOHO CH 2 CH 2 O 1 1 1877 Ph Ph HCOSHO CH 2 CH 2 O 1 1 1878 Ph Ph HCO-----0 0 1879 Ph Ph HCOO Me O--0 1 1880 Ph Ph HCOO Me S--0 1 1881 4-PhPh HHCOOHO CH 2 CH 2 O 1 1 1882 4-PhPh HHCOSHO CH 2 CH 2 O 1 1 1883 4-PhPh HHCO-----0 0 1884 4-PhPh HHCOO Me O--0 1 1885 4-PhPh HHCOO Me S--0 1 1886 2-PhPh HHCOOHO CH 2 CH 2 O 1 1 1887 2-PhPh HHCOSHO CH 2 CH 2 O 1 1 1888 2-PhPh HHCO-----0 0 1889 2-PhPh HHCOO Me O--0 1 1890 2-PhPh HHCOO Me S--0 1 1891 Ph Ph HCSOHO CH 2 CH 2 O 1 1 1892 Ph Ph HCSSHO CH 2 CH 2 O 1 1 1893 Ph Ph HCS-----0 0 1894 Ph Ph HCSO Me O--0 1 1895 Ph Ph HCSO Me S--0 1 1896 Ph Ph Ph C NH OHO CH 2 CH 2 O 1 1 1897 Ph Ph Ph C NH SHO CH 2 CH 2 O 1 1 1898 Ph Ph Ph C NH-----0 0 1899 Ph Ph Ph C NH O Me O--0 1 1900 Ph Ph Ph C NH O Me S--0 1 1901 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 chi 1902 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Chi 1903 3,4-DBP HHCO-----0 0 Chi 1904 3,4-DBP HHCOO Me O--0 1 Chi 1905 3,4-DBP HHCOO Me S--0 1 Chi 1906 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Chi 1907 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Chi 1908 Ph Ph Ph CO-----0 0 Chi 1909 Ph Ph Ph COO Me O--0 1 Chi 1910 Ph Ph Ph COO Me S--0 1 Chi 1911 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Chi 1912 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Chi 1913 3,5-DBP HHCO-----0 0 Chi 1914 3,5-DBP HHCOO Me O--0 1 Chi 1915 3,5-DBP HHCOO Me S--0 1 Chi 1916 3, 4-DBP HHCOOHO CH 2 CH 2 O 1 1 Ri 1917 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Ri 1918 3,4-DBP HHCO-----0 0 Ri 1919 3,4-DBP HHCOO Me O--0 1 Ri 1920 3,4-DBP HHCOO Me S--0 1 Ri 1921 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1922 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Li 1923 Ph Ph Ph CO-----0 0 Li 1924 Ph Ph Ph COO Me O--0 1 Li 1925 Ph Ph Ph COO Me S--0 1 Li 1926 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Ri 1927 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Ri 1928 3,5-DBP HHCO-----0 0 Ri 1929 3,5-DBP HHCOO Me O--0 1 Ri 1930 3,5-DBP HHCOO Me S--0 1 Ri 1931 3, 4-DBP HHCOOHO CH 2 CH 2 O 1 1 Nu 1932 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Nu 1933 3,4-DBP HHCO-----0 0 Nu 1934 3,4-DBP HHCOO Me O--0 1 Nu 1935 3,4-DBP HHCOO Me S--0 1 Nu 1936 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Nu 1937 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Nu 1938 Ph Ph Ph CO-----0 0 Nu 1939 Ph Ph Ph COO Me O--0 1 Nu 1940 Ph Ph Ph COO Me S--0 1 Nu 1941 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Nu 1942 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Nu 1943 3,5-DBP HHCO-----0 0 Nu 1944 3,5-DBP HHCOO Me O--0 1 Nu 1945 3,5-DBP HHCOO Me S--0 1 Nu 1946 3, 4-DBP HHCOOHO CH 2 CH 2 O 1 1 Le 1947 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Le 1948 3,4-DBP HHCO-----0 0 Le 1949 3,4-DBP HHCOO Me O--0 1 Le 1950 3,4-DBP HHCOO Me S--0 1 Le 1951 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Le 1952 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Le 1953 Ph Ph Ph CO-----0 0 Le 1954 Ph Ph Ph COO Me O--0 1 Le 1955 Ph Ph Ph COO Me S--0 1 Le 1956 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Le 1957 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Le 1958 3,5-DBP HHCO-----0 0 Le 1959 3,5-DBP HHCOO Me O--0 1 Le 1960 3,5-DBP HHCOO Me S--0 1 Le 1961 3, 4-DBP HHCO NH Me O CH 2 CH 2 O 1 1 1-1 1962 3,4-DBP HHCOO Ph O--0 1 1-1 1963 3,4-DBP HHCOO 4-ClPh O--0 1 1-1 1964 3,4-DBP HHCO NH 2- NH 2 Et O CH 2 CH 2 O 1 1 1-1 1965 3,4-DBP HHCO NH 2-MeOEt O CH 2 CH 2 O 1 1 1-1 1966 3,4-DBP HHCOS Me O--0 1 1-1 1967 3,4-DBP HHCOSHO--0 1 1-1 1968 3,4-DBP HHCOOHS CH 2 CH 2 O 1 1 1-1 1969 3,4-DBP HHCOO Et O--0 1 1-1 1970 3,4-DBP HHCOO Et S--0 1 1-1 1971 3,4-DBP HHCOO Bu O--0 1 1-1 1972 3,4-DBP HHCOO Bu S--0 1 1-1 1973 3,4-DBP HHCOOHO CH 2 CH 2 O 6 1 1-1 1974 3,4-DBP HHCOOHO CH 2 CH 2 O 6 2 1-1 1975 3,4-DBP HHCOOHO CH 2 CH 2 O 6 3 1-1 1976 3,4-DBP HHCOOHO CH 2 CH 2 O 6 4 1-1 1977 3,4-DBP HHCOOHO 2-OH-PrE NH 1 1 1-1 1978 Ph Ph Ph CO NH Me O CH 2 CH 2 O 1 1 1-1 1979 Ph Ph Ph COO Ph O--0 1 1-1 1980 Ph Ph Ph COO 4-ClPh O--0 1 1-1 1981 Ph Ph Ph CO NH 2-NH 2 Et O CH 2 CH 2 O 1 1 1-1 1982 Ph Ph Ph CO NH 2-MeOEt O CH 2 CH 2 O 1 1 1-1 1983 Ph Ph Ph COS Me O--0 1 1-1 1984 Ph Ph Ph COSHO--0 1 1-1 1985 Ph Ph Ph COOHS CH 2 CH 2 O 1 1 1-1 1986 Ph Ph Ph COO Et O--0 1 1-1 1987 Ph Ph Ph COO Et S--0 1 1-1 1988 Ph Ph Ph COO Bu O--0 1 1-1 1989 Ph Ph Ph COO Bu S--0 1 1-1 1990 Ph Ph Ph COOHO CH 2 CH 2 O 6 1 1-1 1991 Ph Ph Ph COOHO CH 2 CH 2 O 6 2 1-1 1992 Ph Ph Ph COOHO CH 2 CH 2 O 6 3 1-1 1993 Ph Ph Ph COOHO CH 2 CH 2 O 6 4 1-1 1994 Ph Ph Ph COOHO 2-OH-PrE NH 1 1 1-1 1995 3,5-DBP HHCO NH Me O CH 2 CH 2 O 1 1 1-1 1996 3,5-DBP HHCOO Ph O--0 1 1-1 1997 3,5-DBP HHCOO 4-ClPh O--0 1 1-1 1998 3,5-DBP HHCO NH 2- NH 2 Et O CH 2 CH 2 O 1 1 1-1 1999 3,5-DBP HHCO NH 2-MeOEt O CH 2 CH 2 O 1 1 1-1 2000 3,5-DBP HHCOS Me O--0 1 1-1 2001 3,5-DBP HHCOSHO--0 1 1-1 2002 3,5-DBP HHCOOHS CH 2 CH 2 O 1 1 1-1 2003 3,5-DBP HHCOO Et O--0 1 1-1 2004 3,5-DBP HHCOO Et S--0 1 1-1 2005 3,5-DBP HHCOO Bu O--0 1 1-1 2006 3,5-DBP HHCOO Bu S--0 1 1-1 2007 3,5-DBP HHCOOHO CH 2 CH 2 O 6 1 1-1 2008 3,5-DBP HHCOOHO CH 2 CH 2 O 6 2 1-1 2009 3,5-DBP HHCOOHO CH 2 CH 2 O 6 3 1-1 2010 3,5-DBP HHCOOHO CH 2 CH 2 O 6 4 1-1 2011 3,5-DBP HHCOOHO 2-OH-PrE NH 1 1 1-1 2012 3,4-DBP HHCO NH Me O CH 2 CH 2 O 1 1 2013 3,4-DBP HHCOO Ph O--0 1 2014 3,4-DBP HHCOO 4-ClPh O--0 1 2015 3,4-DBP HHCO NH 2-NH 2 Et O CH 2 CH 2 O 1 1 2016 3,4-DBP HHCO NH 2-MeOEt O CH 2 CH 2 O 1 1 2017 3,4-DBP HHCOS Me O--0 1 2018 3,4-DBP HHCOSHO--0 1 2019 3,4-DBP HHCOOHS CH 2 CH 2 O 1 1 2020 3,4-DBP HHCOO Et O--0 1 2021 3,4-DBP HHCOO Et S--0 1 2022 3,4-DBP HHCOO Bu O--0 1 2023 3,4-DBP HHCOO Bu S--0 1 2024 3,4-DBP HHCOOHO CH 2 CH 2 O 6 1 2025 3,4-DBP HHCOOHO CH 2 CH 2 O 6 2 2026 3,4-DBP HHCOOHO CH 2 CH 2 O 6 3 2027 3,4-DBP HHCOOHO CH 2 CH 2 O 6 4 2028 3,4-DBP HHCOOHO 2-OH-PrE NH 1 1 2029 Ph Ph Ph CO NH Me O CH 2 CH 2 O 1 1 2030 Ph Ph Ph COO Ph O--0 1 2031 Ph Ph COO 4-ClPh O--0 1 2032 Ph Ph Ph CO NH 2-NH 2 Et O CH 2 CH 2 O 1 1 2033 Ph Ph Ph CO NH 2-MeOEt O CH 2 CH 2 O 1 1 2034 Ph Ph Ph COS Me O--0 1 2035 Ph Ph Ph COSHO--0 1 2036 Ph Ph Ph COOHS CH 2 CH 2 O 1 1 2037 Ph Ph Ph COO Et O--0 1 2038 Ph Ph COO Et S--0 1 2039 Ph Ph Ph COO Bu O--0 1 2040 Ph Ph Ph COO Bu S--0 1 2041 Ph Ph Ph COOHO CH 2 CH 2 O 6 1 2042 Ph Ph Ph COOHO CH 2 CH 2 O 6 2 2043 Ph Ph Ph COOHO CH 2 CH 2 O 6 3 2044 Ph Ph Ph COOHO CH 2 CH 2 O 6 4 2045 Ph Ph Ph COOHO 2-OH-PrE NH 1 1 2046 3,5-DBP HHCO NH Me O CH 2 CH 2 O 1 1 2047 3,5-DBP HHCOO Ph O--0 1 2048 3,5-DBP HHCOO 4-ClPh O--0 1 2049 3,5-DBP HHCO NH 2-NH 2 Et O CH 2 CH 2 O 1 1 2050 3,5-DBP HHCO NH 2-MeOEt O CH 2 CH 2 O 1 1 2051 3,5-DBP HHCOS Me O--0 1 2052 3,5-DBP HHCOSHO--0 1 2053 3,5-DBP HHCOOHS CH 2 CH 2 O 1 1 2054 3,5-DBP HHCOO Et O--0 1 2055 3,5-DBP HHCOO Et S--0 1 2056 3,5-DBP HHCOO Bu O--0 1 2057 3,5-DBP HHCOO Bu S--0 1 2058 3,5-DBP HHCOOHO CH 2 CH 2 O 6 1 2059 3,5-DBP HHCOOHO CH 2 CH 2 O 6 2 2060 3,5-DBP HHCOOHO CH 2 CH 2 O 6 3 2061 3,5-DBP HHCOOHO CH 2 CH 2 O 6 4 2062 3,5-DBP HHCOOHO 2-OH-PrE NH 1 1 2063 3,4-DBP HHCO NH Me O CH 2 CH 2 O 1 1 3-1 2064 3,4-DBP HHCOO Ph O--0 1 3-1 2065 3,4-DBP HHCOO 4-ClPh O--0 1 3-1 2066 3,4-DBP HHCO NH 2- NH 2 Et O CH 2 CH 2 O 1 1 3-1 2067 3,4-DBP HHCO NH 2-MeOEt O CH 2 CH 2 O 1 1 3-1 2068 3,4-DBP HHCOS Me O--0 1 3-1 2069 3,4-DBP HHCOSHO--0 1 3-1 2070 3,4-DBP HHCOOHS CH 2 CH 2 O 1 1 3-1 2071 3,4-DBP HHCOO Et O--0 1 3-1 2072 3,4-DBP HHCOO Et S--0 1 3-1 2073 3,4-DBP HHCOO Bu O--0 1 3-1 2074 3,4-DBP HHCOO Bu S--0 1 3-1 2075 3,4-DBP HHCOOHO CH 2 CH 2 O 6 1 3-1 2076 3,4-DBP HHCOOHO CH 2 CH 2 O 6 2 3-1 2077 3,4-DBP HHCOOHO CH 2 CH 2 O 6 3 3-1 2078 3,4-DBP HHCOOHO CH 2 CH 2 O 6 4 3-1 2079 3,4-DBP HHCOOHO 2-OH-PrE NH 1 1 3-1 2080 Ph Ph Ph CO NH Me O CH 2 CH 2 O 1 1 3-1 2081 Ph Ph Ph COO Ph O--0 1 3-1 2082 Ph Ph Ph COO 4-ClPh O--0 1 3-1 2083 Ph Ph Ph CO NH 2-NH 2 Et O CH 2 CH 2 O 1 1 3-1 2084 Ph Ph Ph CO NH 2-MeOEt O CH 2 CH 2 O 1 1 3-1 2085 Ph Ph Ph COS Me O--0 1 3-1 2086 Ph Ph Ph COSHO--0 1 3-1 2087 Ph Ph Ph COOHS CH 2 CH 2 O 1 1 3-1 2088 Ph Ph Ph COO Et O--0 1 3-1 2089 Ph Ph Ph COO Et S--0 1 3-1 2090 Ph Ph Ph COO Bu O--0 1 3-1 2091 Ph Ph Ph COO Bu S--0 1 3-1 2092 Ph Ph Ph COOHO CH 2 CH 2 O 6 1 3-1 2093 Ph Ph Ph COOHO CH 2 CH 2 O 6 2 3-1 2094 Ph Ph Ph COOHO CH 2 CH 2 O 6 3 3-1 2095 Ph Ph Ph COOHO CH 2 CH 2 O 6 4 3-1 2096 Ph Ph Ph COOHO 2-OH-PrE NH 1 1 3-1 2097 3,5-DBP HHCO NH Me O CH 2 CH 2 O 1 1 3-1 2098 3,5-DBP HHCOO Ph O--0 1 3-1 2099 3,5-DBP HHCOO 4-ClPh O--0 1 3-1 2100 3,5-DBP HHCO NH 2- NH 2 Et O CH 2 CH 2 O 1 1 3-1 2101 3,5-DBP HHCO NH 2-MeOEt O CH 2 CH 2 O 1 1 3-1 2102 3,5-DBP HHCOS Me O--0 1 3-1 2103 3,5-DBP HHCOSHO--0 1 3-1 2104 3,5-DBP HHCOOHS CH 2 CH 2 O 1 1 3-1 2105 3,5-DBP HHCOO Et O--0 1 3-1 2106 3,5-DBP HHCOO Et S--0 1 3-1 2107 3,5-DBP HHCOO Bu O--0 1 3-1 2108 3,5-DBP HHCOO Bu S--0 1 3-1 2109 3,5-DBP HHCOOHO CH 2 CH 2 O 6 1 3-1 2110 3,5-DBP HHCOOHO CH 2 CH 2 O 6 2 3-1 2111 3,5-DBP HHCOOHO CH 2 CH 2 O 6 3 3-1 2112 3,5-DBP HHCOOHO CH 2 CH 2 O 6 4 3-1 2113 3,5-DBP HHCOOHO 2-OH-PrE NH 1 1 3-1 2114 3,4-DBP HHCO NH Me O CH 2 CH 2 O 1 1 2115 3,4-DBP HHCOO Ph O--0 1 2116 3,4-DBP HHCOO 4-ClPh O--0 1 2117 3,4-DBP HHCO NH 2-NH 2 Et O CH 2 CH 2 O 1 1 2118 3,4-DBP HHCO NH 2-MeOEt O CH 2 CH 2 O 1 1 2119 3,4-DBP HHCOS Me O--0 1 2120 3,4-DBP HHCOSHO--0 1 2121 3,4-DBP HHCOOHS CH 2 CH 2 O 1 1 2122 3,4-DBP HHCOO Et O--0 1 2123 3,4-DBP HHCOO Et S--0 1 2124 3,4-DBP HHCOO Bu O--0 1 2125 3,4-DBP HHCOO Bu S--0 1 2126 3,4-DBP HHCOOHO CH 2 CH 2 O 6 1 2127 3,4-DBP HHCOOHO CH 2 CH 2 O 6 2 2128 3,4-DBP HHCOOHO CH 2 CH 2 O 6 3 2129 3,4-DBP HHCOOHO CH 2 CH 2 O 6 4 2130 3,4-DBP HHCOOHO 2-OH-PrE NH 1 1 2131 Ph Ph Ph CO CO Me O CH 2 CH 2 O 1 1 2132 Ph Ph Ph COO Ph O--0 1 2133 Ph Ph COO 4-ClPh O--0 1 2134 Ph Ph Ph CO NH 2-NH 2 Et O CH 2 CH 2 O 1 1 2135 Ph Ph Ph CO NH 2-MeOEt O CH 2 CH 2 O 1 1 2136 Ph Ph Ph COS Me O--0 1 2137 Ph Ph COSHO--0 1 2138 Ph Ph Ph COOHS CH 2 CH 2 O 1 1 2139 Ph Ph Ph COO Et O--0 1 2140 Ph Ph Ph COO Et S--0 1 2141 Ph Ph Ph COO Bu O--0 1 2142 Ph Ph Ph COO Bu S--0 1 2143 Ph Ph Ph COOHO CH 2 CH 2 O 6 1 2144 Ph Ph Ph COOHO CH 2 CH 2 O 6 2 2145 Ph Ph Ph COOHO CH 2 CH 2 O 6 3 2146 Ph Ph Ph COOHO CH 2 CH 2 O 6 4 2147 Ph Ph Ph COOHO 2-OH-PrE NH 1 1 2148 3,5-DBP HHCO NH Me O CH 2 CH 2 O 1 1 2149 3,5-DBP HHCOO Ph O--0 1 2150 3,5-DBP HHCOO 4-ClPh O--0 1 2151 3,5-DBP HHCO NH 2-NH 2 Et O CH 2 CH 2 O 1 1 2152 3,5-DBP HHCO NH 2-MeOEt O CH 2 CH 2 O 1 1 2153 3,5-DBP HHCOS Me O--0 1 2154 3,5-DBP HHCOSHO--0 1 2155 3,5-DBP HHCOOHS CH 2 CH 2 O 1 1 2156 3,5-DBP HHCOO Et O--0 1 2157 3,5-DBP HHCOO Et S--0 1 2158 3,5-DBP HHCOO Bu O--0 1 2159 3,5-DBP HHCOO Bu S--0 1 2160 3,5-DBP HHCOOHO CH 2 CH 2 O 6 1 2161 3,5-DBP HHCOOHO CH 2 CH 2 O 6 2 2162 3,5-DBP HHCOOHO CH 2 CH 2 O 6 3 2163 3,5-DBP HHCOOHO CH 2 CH 2 O 6 4 2164 3,5-DBP HHCOOHO 2-OH-PrE NH 1 1 2165 4-MePh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2166 4-MePh 4-MePh Ph COOHO CH 2 CH 2 O 1 1 1-1 2167 4-MePh 4-MePh 4-MePh COOHO CH 2 CH 2 O 1 1 1-1 2168 4-tBuPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2169 4-tBuPh 4-tBuPh Ph COOHO CH 2 CH 2 O 1 1 1-1 2170 4-tBuPh 4-tBuPh 4-tBuPh COOHO CH 2 CH 2 O 1 1 1-1 2171 4-NO 2 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2172 4-NO 2 Ph 4-NO 2 Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2173 4-FPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2174 4-FPh 4-FPh Ph COOHO CH 2 CH 2 O 1 1 1-1 2175 2,4-F 2 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2176 2-ClPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2177 4-ClPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2178 4-ClPh 4-ClPh Ph COOHO CH 2 CH 2 O 1 1 1-1 2179 4-BrPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2180 4-BrPh 4-BrPh Ph COOHO CH 2 CH 2 O 1 1 1-1 2181 4-IPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2182 4-tBuOPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2183 4-EtOPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2184 4-EtOPh 4-EtOPh Ph COOHO CH 2 CH 2 O 1 1 1-1 2185 2-BnOPh HHCOOHO CH 2 CH 2 O 1 1 1-1 2186 4-BnOPh Ph Ph COOHO CH 2 CH 2 O 1 1 1-1 2187 4-BnOPh 4-BnOPh Ph COOHO CH 2 CH 2 O 1 1 1-1 2188 4-MeOPh 4-MeOPh 4-MeOPh COOHO CH 2 CH 2 O 1 1 1-1 2189 9-ANT HHCOOHO CH 2 CH 2 O 1 1 1-1 2190 2-ANT HHCOOHO CH 2 CH 2 O 1 1 1-1 2191 1-NAP HHCOOHO CH 2 CH 2 O 1 1 1-1 2192 3-PhOPh HHCOOHO CH 2 CH 2 O 1 1 1-1 2193 4-PhOPh HHCOOHO CH 2 CH 2 O 1 1 1-1 2194 2-ANQ HHCOOHO CH 2 CH 2 O 1 1 1-1 2195 4-PHE HHCOOHO CH 2 CH 2 O 1 1 1-1 2196 3,4-DBP HHCOSHO CH 2 CH 2 O 6 1 1-1 2197 3,4-DBP HHCO NH Et O CH 2 CH 2 O 6 1 1-1 2198 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 6 1 1-1 2199 3,4-DBP HHCO NH 2-NH 2 Et O CH 2 CH 2 O 6 1 1-1 2200 3,4-DBP HHCOOHO CH 2 CH 2 O 2 1 1-1 2201 3,4-DBP HHCOSHO CH 2 CH 2 O 2 1 1-1 2202 3,4-DBP HHCOO 2-NO 2 Ph O--0 1 1-1 2203 3,4-DBP HHCOO 4-NO 2 Ph O--0 1 1-1 2204 3,4-DBP HHCOO 2-FPh O--0 1 1-1 2205 3,4-DBP HHCOO 2-BrPh O--0 1 1-1 2206 3,4- DBP HHCOO 2-IPh O--0 1 1-1 2207 3,4-DBP HHCOO 4-MeOPh O--0 1 1-1 2208 3,4-DBP HHCOO 4-MeSPh O--0 1 1-1 2209 3,4-DBP HHCOO 4-EtOPh O--0 1 1-1 2210 3,4-DBP HHCOOHO (CH 2 ) 3 O 1 1 1-1 2211 3,4-DBP HHCOOHO (CH 2 ) Four O 1 1 1-1 2212 3,4-DBP HHCOOHO (CH 2 ) Five O 1 1 1-1 2213 3,4-DBP HHCOOHO (CH 2 ) 6 O 1 1 1-1 2214 3,4-DBP HHCOOHO (CH 2 ) 7 O 1 1 1-1 2215 3,4-DBP HHCOOHO (CH 2 ) 8 O 1 1 1-1 2216 3,4-DBP HHCOOHO (CH 2 ) 9 O 1 1 1-1 2217 3,4-DBP HHCOOHO (CH 2 ) Ten O 1 1 1-1 2218 3,4-DBP HHCOOHO CH 2 CH (CH 3 ) O 1 1 1-1 2219 3,4-DBP HHCOOHO 1-Me-PrE O 1 1 1-1 2220 3,4-DBP HHCOOHO 2-Me-BuE O 1 1 1-1 2221 3,4-DBP HHCOSHO (CH2) 3 O 1 1 1-1 2222 3,4-DBP HHCOSHO (CH2) Four O 1 1 1-1 2223 3,4-DBP HHCOSHO (CH2) Five O 1 1 1-1 2224 3,4-DBP HHCOSHO (CH2) 6 O 1 1 1-1 2225 3,4-DBP HHCOSHO (CH2) 7 O 1 1 1-1 2226 3,4-DBP HHCOSHO (CH2) 8 O 1 1 1-1 2227 3,4-DBP HHCOSHO (CH2) 9 O 1 1 1-1 2228 3,4-DBP HHCOSHO (CH2) Ten O 1 1 1-1 2229 3,4-DBP HHCOSHO CH 2 CH (CH 3 ) O 1 1 1-1 2230 3,4-DBP HHCOSHO 1-Me-PrE O 1 1 1-1 2231 3,4-DBP HHCOSHO 2-Me-BuE O 1 1 1-1 2232 3,4-DBP HHCO NH Ph O CH 2 CH 2 O 1 1 1-1 2233 3,4-DBP HHCO NH 2-ClPh O CH 2 CH 2 O 1 1 1-1 2234 3,4-DBP HHCO NH Me O (CH 2 ) 3 O 1 1 1-1 2235 3,4-DBP HHCO NH Pr O (CH 2 ) 3 O 1 1 1-1 2236 3,4-DBP HHCO NH 2-NH 2 Et O (CH 2 ) 3 O 1 1 1-1 2237 3,4-DBP HHCO NH 2-MeOEt O (CH 2 ) 3 O 1 1 1-1 2238 3,4-DBP HHCO NH Ph O (CH 2 ) 3 O 1 1 1-1 2239 3,4-DBP HHCO NH 2-ClPh O (CH 2 ) 3 O 1 1 1-1 2240 3,4-DBP HHCO NH Pr O (CH 2 ) Four O 1 1 1-1 2241 3,4-DBP HHCO NH Pr O (CH 2 ) Five O 1 1 1-1 2242 3,4-DBP HHCO NH Pr O (CH 2 ) 6 O 1 1 1-1 2243 3,4-DBP HHCO NH Pr O (CH 2 ) 7 O 1 1 1-1 2244 3,4-DBP HHCO NH Pr O (CH 2 ) 8 O 1 1 1-1 2245 3,4-DBP HHCO NH Pr O (CH 2 ) 9 O 1 1 1-1 2246 3,4-DBP HHCO NH Pr O (CH 2 ) Ten O 1 1 1-1 2247 3,4-DBP HHCO NH Pr O CH 2 CH (CH 3 ) O 1 1 1-1 2248 3,4-DBP HHCO NH Pr O 1-Me-PrE O 1 1 1-1 2249 3,4-DBP HHCO NH Pr O 2-Me-BuE O 1 1 1-1 2250 Ph Ph Ph C NH OHO CH 2 CH 2 O 6 1 1-1 2251 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 wo 2252 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 wo 2253 3,4-DBP HHCO-----0 0 wo 2254 3,4-DBP HHCOO Me O--0 1 wo 2255 3,4-DBP HHCOO Me S--0 1 wo 2256 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 wo 2257 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 wo 2258 Ph Ph Ph CO-----0 0 wo 2259 Ph Ph Ph COO Me O--0 1 wo 2260 Ph Ph Ph COO Me S--0 1 wo 2261 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 wo 2262 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 wo 2263 3,5-DBP HHCO-----0 0 wo 2264 3,5-DBP HHCOO Me O--0 1 wo 2265 3,5-DBP HHCOO Me S--0 1 wo 2266 3, 4-DBP HHCOOHO CH 2 CH 2 O 1 1 Wa 2267 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Wa 2268 3,4-DBP HHCO-----0 0 Wa 2269 3,4-DBP HHCOO Me O--0 1 Wa 2270 3,4-DBP HHCOO Me S--0 1 Wa 2271 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Wa 2272 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Wa 2273 Ph Ph Ph CO-----0 0 Wa 2274 Ph Ph Ph COO Me O--0 1 Wa 2275 Ph Ph Ph COO Me S--0 1 Wa 2276 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Wa 2277 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Wa 2278 3,5-DBP HHCO-----0 0 Wa 2279 3,5-DBP HHCOO Me O--0 1 Wa 2280 3,5-DBP HHCOO Me S--0 1 Wa 2281 3, 4-DBP HHCOOHO CH 2 CH 2 O 1 1 Car 2282 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 2283 3,4-DBP HHCO-----0 0 2 2 4, 3,4-DBP HHCOO Me O--0 1 2285 3,4-DBP HHCOO Me S--0 1 2286 Ph Ph Ph COOHO CH 2 CH 2 O 11 Ka 2287 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Car 2288 Ph Ph Ph CO-----0 0 Car 2289 Ph Ph Ph COO Me O--0 1 Car 2290 Ph Ph Ph COO Me S--0 1 Car 2291 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Power 2292 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 2293 3,5-DBP HHCO-----0 0 2 9 3,5-DBP HHCOO Me O--0 1 2295 3,5-DBP HHCOO Me S--0 1 2296 3, 4-DBP HHCOOHO CH 2 CH 2 O 1 1 Yo 2297 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Yo 2298 3,4-DBP HHCO-----0 0 Yo 2299 3,4-DBP HHCOO Me O--0 1 Yo 2300 3,4-DBP HHCOO Me S--0 1 Yo 2301 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 Yo 2302 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Yo 2303 Ph Ph Ph CO-----0 0 Yo 2304 Ph Ph Ph COO Me O--0 1 Yo 2305 Ph Ph Ph COO Me S--0 1 Yo 2306 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 Yo 2307 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 Yo 2308 3,5-DBP HHCO-----0 0 Yo 2309 3,5-DBP HHCOO Me O--0 1 Yo 2310 3,5-DBP HHCOO Me S--0 1 Yo 2311 3, 4-DBP HHCOOHO CH 2 CH 2 O 1 1 23 23 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 Ta 2313 3,4-DBP HHCO-----0 0 Ta 2314 3,4-DBP HHCOO Me O--0 1 Ta 2315 3,4-DBP HHCOO Me S--0 1 Ta 2316 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 2 3 2 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 Ta 2318 Ph Ph Ph CO-----0 0 Ta 2319 Ph Ph Ph COO Me O--0 1 Ta 2320 Ph Ph Ph COO Me S--0 1 Ta 2321 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 2322 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 2323 3,5-DBP HHCO-----0 0 Ta 2324 3,5-DBP HHCOO Me O--0 1 Ta 2325 3,5-DBP HHCOO Me S--0 1 Ta 2326 4- MeOPh 4-MeOPh Ph CO-----0 0 CH 2327 4-MeOPh 4-MeOPh Ph CO-----0 0 RE 2328 4-MeOPh 4-MeOPh Ph CO-----0 0 Nu 2329 4 -MeOPh 4-MeOPh Ph CO-----0 0 2323 4-MeOPh 4-MeOPh Ph CO-----0 0 2331 4-MeOPh 4-MeOPh Ph CO-----0 0 WA 2332 4-MeOPh 4-MeOPh Ph CO-----0 0 F 2333 4-MeOPh 4-MeOPh Ph CO-----0 0 Yo 2334 4-MeOPh 4-MeOPh Ph CO-----0 0 2335 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 a-1 2336 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 a-1 2337 3,4-DBP HHCO-----0 0 a-1 2338 3,4-DBP HHCOO Me O--0 1 a-1 2339 3,4-DBP HHCOO Me S-- 0 1 a-1 2340 3,4-DBP HHCOO 2-ClPh O--0 1 a-1 2341 3,4-DBP HHCO CH 2 HO--0 1 a-1 2342 3,4-DBP HHCO CH 2 HS--0 1 a-1 2343 3,4-DBP HHCO PhE HO--0 1 a-1 2344 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 a-1 2345 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 a-1 2346 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 a-1 2347 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 a-1 2348 Ph Ph Ph CO-----0 0 a-1 2349 Ph Ph Ph COO Me O--0 1 a-1 2350 Ph Ph COO Me S--0 1 a-1 2351 Ph Ph Ph COO 2-ClPh O--0 1 a-1 2352 Ph Ph Ph CO CH 2 HO--0 1 a-1 2353 Ph Ph Ph CO CH 2 HS--0 1 a-1 2354 Ph Ph Ph CO PhE HO--0 1 a-1 2355 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 a-1 2356 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 a-1 2357 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 a-1 2358 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 a-1 2359 3,5-DBP HHCO-----0 0 a-1 2360 3,5-DBP HHCOO Me O--0 1 a-1 2361 3,5-DBP HHCOO Me S-- 0 1 a-1 2362 3,5-DBP HHCOO 2-ClPh O--0 1 a-1 2363 3,5-DBP HHCO CH 2 HO--0 1 a-1 2364 3,5-DBP HHCO CH 2 HS--0 1 a-1 2365 3,5-DBP HHCO PhE HO--0 1 a-1 2366 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 a-1 2367 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 a-1 2368 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 a-1 2369 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 a-1 2370 4-MeOPh 4-MeOPh Ph CO-----0 0 a-1 2371 4-MeOPh 4-MeOPh Ph COO Me O--0 1 a-1 2372 4-MeOPh 4-MeOPh Ph COO Me S--0 1 a-1 2373 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 a-1 2374 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 a-1 2375 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 a-1 2376 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 a-1 2377 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 a-1 2378 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 a-1 2379 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 a-1 2380 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 a-1 2381 4-MeOPh Ph Ph CO-----0 0 a-1 2382 4-MeOPh Ph Ph COO Me O--0 1 a-1 2383 4-MeOPh Ph Ph COO Me S-- 0 1 a-1 2384 4-MeOPh Ph Ph COO 2-ClPh O--0 1 a-1 2385 4-MeOPh Ph Ph CO CH 2 HO--0 1 a-1 2386 4-MeOPh Ph Ph CO CH 2 HS--0 1 a-1 2387 4-MeOPh Ph Ph CO PhE HO--0 1 a-1 2388 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 a-1 2389 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 a-1 2390 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 a-1 2391 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 a-1 2393 tBu Ph Ph Si OO Me O--0 1 a-1 2394 tBu Ph Ph Si OO Me S--0 1 a-1 2395 tBu Ph Ph Si OO 2-ClPh O--0 1 a-1 2396 tBu Ph Ph Si O CH 2 HO--0 1 a-1 2397 tBu Ph Ph Si O CH 2 HS--0 1 a-1 2398 tBu Ph Ph Si O PhE HO--0 1 a-1 2399 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 a-1 2400 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 a-1 2401 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 a-1 2402 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 a-1 2403 Ph Ph Ph CS-----0 0 a-1 2404 Ph Ph Ph CSO Me O--0 1 a-1 2405 Ph Ph Ph CSO Me S--0 1 a-1 2406 Ph Ph Ph CSO 2-ClPh O--0 1 a-1 2407 Ph Ph Ph CS CH 2 HO--0 1 a-1 2408 Ph Ph Ph CS CH 2 HS--0 1 a-1 2409 Ph Ph Ph CS PhE HO--0 1 a-1 2410 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 a-1 2411 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 a-1 2412 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 a-1 2413 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 a-1 2414 4-BnOPh HHCO-----0 0 a-1 2415 4-BnOPh HHCOO Me O--0 1 a-1 2416 4-BnOPh HHCOO Me S--0 1 a-1 2417 4-BnOPh HHCOO 2-ClPh O--0 1 a-1 2418 4-BnOPh HHCO CH 2 HO--0 1 a-1 2419 4-BnOPh HHCO CH 2 HS--0 1 a-1 2420 4-BnOPh HHCO PhE HO--0 1 a-1 2421 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 a-1 2422 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 a-1 2423 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 a-1 2424 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 a-1 2425 Ph Xanthen-9-yl O-----0 0 a-1 2426 Ph Xanthen-9-yl OO Me O--0 1 a-1 2427 Ph Xanthen-9-yl OO Me S--0 1 a-1 2428 Ph Xanthen-9-yl OO 2-ClPh O--0 1 a-1 2429 Ph Xanthen-9-yl O CH 2 HO--0 1 a-1 2430 Ph Xanthen-9-yl O CH 2 HS--0 1 a-1 2431 Ph Xanthen-9-yl O PhE HO--0 1 a-1 2432 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 a-1 2433 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 a-1 2434 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 a-1 2435 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 a-1 2436 Ph Fluoren-9-yl O-----0 0 a-1 2437 Ph Fluoren-9-yl OO Me O--0 1 a-1 2438 Ph Fluoren-9-yl OO Me S--0 1 a-1 2439 Ph Fluoren-9-yl OO 2-ClPh O--0 1 a-1 2440 Ph Fluoren-9-yl O CH 2 HO--0 1 a-1 2441 Ph Fluoren-9-yl O CH 2 HS--0 1 a-1 2442 Ph Fluoren-9-yl O PhE HO--0 1 a-1 2443 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 a-1 2444 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 a-1 2445 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 b-1 2446 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 b-1 2447 3,4-DBP HHCO-----0 0 b-1 2448 3,4-DBP HHCOO Me O--0 1 b-1 2449 3,4-DBP HHCOO Me S-- 0 1 b-1 2450 3,4-DBP HHCOO 2-ClPh O--0 1 b-1 2451 3,4-DBP HHCO CH 2 HO--0 1 b-1 2452 3,4-DBP HHCO CH 2 HS--0 1 b-1 2453 3,4-DBP HHCO PhE HO--0 1 b-1 2454 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 b-1 2455 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 b-1 2456 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 b-1 2457 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 b-1 2458 Ph Ph Ph CO-----0 0 b-1 2459 Ph Ph Ph COO Me O--0 1 b-1 2460 Ph Ph Ph COO Me S--0 1 b-1 2461 Ph Ph Ph COO 2-ClPh O--0 1 b-1 2462 Ph Ph Ph CO CH 2 HO--0 1 b-1 2463 Ph Ph Ph CO CH 2 HS--0 1 b-1 2464 Ph Ph Ph CO PhE HO--0 1 b-1 2465 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 b-1 2466 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 b-1 2467 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 b-1 2468 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 b-1 2469 3,5-DBP HHCO-----0 0 b-1 2470 3,5-DBP HHCOO Me O--0 1 b-1 2471 3,5-DBP HHCOO Me S-- 0 1 b-1 2472 3,5-DBP HHCOO 2-ClPh O--0 1 b-1 2473 3,5-DBP HHCO CH 2 HO--0 1 b-1 2474 3,5-DBP HHCO CH 2 HS--0 1 b-1 2475 3,5-DBP HHCO PhE HO--0 1 b-1 2476 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 b-1 2477 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 b-1 2478 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 b-1 2479 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 b-1 2480 4-MeOPh 4-MeOPh Ph CO-----0 0 b-1 2481 4-MeOPh 4-MeOPh Ph COO Me O--0 1 b-1 2482 4-MeOPh 4-MeOPh Ph COO Me S--0 1 b-1 2483 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 b-1 2484 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 b-1 2485 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 b-1 2486 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 b-1 2487 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 b-1 2488 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 b-1 2489 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 b-1 2490 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 b-1 2491 4-MeOPh Ph Ph CO-----0 0 b-1 2492 4-MeOPh Ph Ph COO Me O--0 1 b-1 2493 4-MeOPh Ph Ph COO Me S-- 0 1 b-1 2494 4-MeOPh Ph Ph COO 2-ClPh O--0 1 b-1 2495 4-MeOPh Ph Ph CO CH 2 HO--0 1 b-1 2496 4-MeOPh Ph Ph CO CH 2 HS--0 1 b-1 2497 4-MeOPh Ph Ph CO PhE HO--0 1 b-1 2498 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 b-1 2499 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 b-1 2500 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 b-1 2501 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 b-1 2502 tBu Ph Ph Si O-----0 0 b-1 2503 tBu Ph Ph Si OO Me O--0 1 b-1 2504 tBu Ph Ph Si OO Me S--0 1 b -1 2505 tBu Ph Ph Si OO 2-ClPh O--0 1 b-1 2506 tBu Ph Ph Si O CH 2 HO--0 1 b-1 2507 tBu Ph Ph Si O CH 2 HS--0 1 b-1 2508 tBu Ph Ph Si O PhE HO--0 1 b-1 2509 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 b-1 2510 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 b-1 2511 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 b-1 2512 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 b-1 2513 Ph Ph Ph CS-----0 0 b-1 2514 Ph Ph Ph CSO Me O--0 1 b-1 2515 Ph Ph Ph CSO Me S--0 1 b-1 2516 Ph Ph Ph CSO 2-ClPh O--0 1 b-1 2517 Ph Ph Ph CS CH 2 HO--0 1 b-1 2518 Ph Ph Ph CS CH 2 HS--0 1 b-1 2519 Ph Ph Ph CS PhE HO--0 1 b-1 2520 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 b-1 2521 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 b-1 2522 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 b-1 2523 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 b-1 2524 4-BnOPh HHCO-----0 0 b-1 2525 4-BnOPh HHCOO Me O--0 1 b-1 2526 4-BnOPh HHCOO Me S--0 1 b-1 2527 4-BnOPh HHCOO 2-ClPh O--0 1 b-1 2528 4-BnOPh HHCO CH 2 HO--0 1 b-1 2529 4-BnOPh HHCO CH 2 HS--0 1 b-1 2530 4-BnOPh HHCO PhE HO--0 1 b-1 2531 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 b-1 2532 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 b-1 2533 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 b-1 2534 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 b-1 2535 Ph Xanthen-9-yl O-----0 0 b-1 2536 Ph Xanthen-9-yl OO Me O--0 1 b-1 2537 Ph Xanthen-9-yl OO Me S--0 1 b-1 2538 Ph Xanthen-9-yl OO 2-ClPh O--0 1 b-1 2539 Ph Xanthen-9-yl O CH 2 HO--0 1 b-1 2540 Ph Xanthen-9-yl O CH 2 HS--0 1 b-1 2541 Ph Xanthen-9-yl O PhE HO--0 1 b-1 2542 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 b-1 2543 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 b-1 2544 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 b-1 2545 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 b-1 2546 Ph Fluoren-9-yl O-----0 0 b-1 2547 Ph Fluoren-9-yl OO Me O--0 1 b-1 2548 Ph Fluoren-9-yl OO Me S--0 1 b-1 2549 Ph Fluoren-9-yl OO 2-ClPh O--0 1 b-1 2550 Ph Fluoren-9-yl O CH 2 HO--0 1 b-1 2551 Ph Fluoren-9-yl O CH 2 HS--0 1 b-1 2552 Ph Fluoren-9-yl O PhE HO--0 1 b-1 2553 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 b-1 2554 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 b-1 2555 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 c-1 2556 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 c-1 2557 3,4-DBP HHCO-----0 0 c-1 2558 3,4-DBP HHCOO Me O--0 1 c-1 2559 3,4-DBP HHCOO Me S-- 0 1 c-1 2560 3,4-DBP HHCOO 2-ClPh O--0 1 c-1 2561 3,4-DBP HHCO CH 2 HO--0 1 c-1 2562 3,4-DBP HHCO CH 2 HS--0 1 c-1 2563 3,4-DBP HHCO PhE HO--0 1 c-1 2564 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 c-1 2565 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 c-1 2566 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 c-1 2567 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 c-1 2568 Ph Ph Ph CO-----0 0 c-1 2569 Ph Ph Ph COO Me O--0 1 c-1 2570 Ph Ph Ph COO Me S--0 1 c-1 2571 Ph Ph Ph COO 2-ClPh O--0 1 c-1 2572 Ph Ph Ph CO CH 2 HO--0 1 c-1 2573 Ph Ph Ph CO CH 2 HS--0 1 c-1 2574 Ph Ph Ph CO PhE HO--0 1 c-1 2575 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 c-1 2576 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 c-1 2577 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 c-1 2578 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 c-1 2579 3,5-DBP HHCO-----0 0 c-1 2580 3,5-DBP HHCOO Me O--0 1 c-1 2581 3,5-DBP HHCOO Me S-- 0 1 c-1 2582 3,5-DBP HHCOO 2-ClPh O--0 1 c-1 2583 3,5-DBP HHCO CH 2 HO--0 1 c-1 2584 3,5-DBP HHCO CH 2 HS--0 1 c-1 2585 3,5-DBP HHCO PhE HO--0 1 c-1 2586 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 c-1 2587 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 c-1 2588 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 c-1 2589 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 c-1 2590 4-MeOPh 4-MeOPh Ph CO-----0 0 c-1 2591 4-MeOPh 4-MeOPh Ph COO Me O--0 1 c-1 2592 4-MeOPh 4-MeOPh Ph COO Me S--0 1 c-1 2593 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 c-1 2594 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 c-1 2595 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 c-1 2596 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 c-1 2597 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 c-1 2598 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 c-1 2599 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 c-1 2600 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 c-1 2601 4-MeOPh Ph Ph CO-----0 0 c-1 2602 4-MeOPh Ph Ph COO Me O--0 1 c-1 2603 4-MeOPh Ph Ph COO Me S-- 0 1 c-1 2604 4-MeOPh Ph Ph COO 2-ClPh O--0 1 c-1 2605 4-MeOPh Ph Ph CO CH 2 HO--0 1 c-1 2606 4-MeOPh Ph Ph CO CH 2 HS--0 1 c-1 2607 4-MeOPh Ph Ph CO PhE HO--0 1 c-1 2608 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 c-1 2609 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 c-1 2610 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 c-1 2611 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 c-1 2612 tBu Ph Ph Si O-----0 0 c-1 2613 tBu Ph Ph Si OO Me O--0 1 c-1 2614 tBu Ph Ph Si OO Me S--0 1 c -1 2615 tBu Ph Ph Si OO 2-ClPh O--0 1 c-1 2616 tBu Ph Ph Si O CH 2 HO--0 1 c-1 2617 tBu Ph Ph Si O CH 2 HS--0 1 c-1 2618 tBu Ph Ph Si O PhE HO--0 1 c-1 2619 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 c-1 2620 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 c-1 2621 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 c-1 2622 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 c-1 2623 Ph Ph Ph CS-----0 0 c-1 2624 Ph Ph Ph CSO Me O--0 1 c-1 2625 Ph Ph Ph CSO Me S--0 1 c-1 2626 Ph Ph Ph CSO 2-ClPh O--0 1 c-1 2627 Ph Ph Ph CS CH 2 HO--0 1 c-1 2628 Ph Ph Ph CS CH 2 HS--0 1 c-1 2629 Ph Ph Ph CS PhE HO--0 1 c-1 2630 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 c-1 2631 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 c-1 2632 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 c-1 2633 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 c-1 2634 4-BnOPh HHCO-----0 0 c-1 2635 4-BnOPh HHCOO Me O--0 1 c-1 2636 4-BnOPh HHCOO Me S--0 1 c-1 2637 4-BnOPh HHCOO 2-ClPh O--0 1 c-1 2638 4-BnOPh HHCO CH 2 HO--0 1 c-1 2639 4-BnOPh HHCO CH 2 HS--0 1 c-1 2640 4-BnOPh HHCO PhE HO--0 1 c-1 2641 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 c-1 2642 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 c-1 2643 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 c-1 2644 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 c-1 2645 Ph Xanthen-9-yl O-----0 0 c-1 2646 Ph Xanthen-9-yl OO Me O--0 1 c-1 2647 Ph Xanthen-9-yl OO Me S--0 1 c-1 2648 Ph Xanthen-9-yl OO 2-ClPh O--0 1 c-1 2649 Ph Xanthen-9-yl O CH 2 HO--0 1 c-1 2650 Ph Xanthen-9-yl O CH 2 HS--0 1 c-1 2651 Ph Xanthen-9-yl O PhE HO--0 1 c-1 2652 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 c-1 2653 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 c-1 2654 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 c-1 2655 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 c-1 2656 Ph Fluoren-9-yl O-----0 0 c-1 2657 Ph Fluoren-9-yl OO Me O--0 1 c-1 2658 Ph Fluoren-9-yl OO Me S--0 1 c-1 2659 Ph Fluoren-9-yl OO 2-ClPh O--0 1 c-1 2660 Ph Fluoren-9-yl O CH 2 HO--0 1 c-1 2661 Ph Fluoren-9-yl O CH 2 HS--0 1 c-1 2662 Ph Fluoren-9-yl O PhE HO--0 1 c-1 2663 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 c-1 2664 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 c-1 2665 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 d-1 2666 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 d-1 2667 3,4-DBP HHCO-----0 0 d-1 2668 3,4-DBP HHCOO Me O--0 1 d-1 2669 3,4-DBP HHCOO Me S-- 0 1 d-1 2670 3,4-DBP HHCOO 2-ClPh O--0 1 d-1 2671 3,4-DBP HHCO CH 2 HO--0 1 d-1 2672 3,4-DBP HHCO CH 2 HS--0 1 d-1 2673 3,4-DBP HHCO PhE HO--0 1 d-1 2674 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 d-1 2675 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 d-1 2676 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 d-1 2677 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 d-1 2678 Ph Ph Ph CO-----0 0 d-1 2679 Ph Ph Ph COO Me O--0 1 d-1 2680 Ph Ph Ph COO Me S--0 1 d-1 2681 Ph Ph Ph COO 2-ClPh O--0 1 d-1 2682 Ph Ph Ph CO CH 2 HO--0 1 d-1 2683 Ph Ph Ph CO CH 2 HS--0 1 d-1 2684 Ph Ph Ph CO PhE HO--0 1 d-1 2685 Ph Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 d-1 2686 Ph Ph Ph COO Me NH (CH 2 ) 3 -1 1 d-1 2687 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 d-1 2688 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 d-1 2689 3,5-DBP HHCO-----0 0 d-1 2690 3,5-DBP HHCOO Me O--0 1 d-1 2691 3,5-DBP HHCOO Me S-- 0 1 d-1 2692 3,5-DBP HHCOO 2-ClPh O--0 1 d-1 2693 3,5-DBP HHCO CH 2 HO--0 1 d-1 2694 3,5-DBP HHCO CH 2 HS--0 1 d-1 2695 3,5-DBP HHCO PhE HO--0 1 d-1 2696 3,5-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 d-1 2697 3,5-DBP HHCOO Me NH (CH 2 ) 3 -1 1 d-1 2698 4-MeOPh 4-MeOPh Ph COOHO CH 2 CH 2 O 1 1 d-1 2699 4-MeOPh 4-MeOPh Ph COSHO CH 2 CH 2 O 1 1 d-1 2700 4-MeOPh 4-MeOPh Ph CO-----0 0 d-1 2701 4-MeOPh 4-MeOPh Ph COO Me O--0 1 d-1 2702 4-MeOPh 4-MeOPh Ph COO Me S--0 1 d-1 2703 4-MeOPh 4-MeOPh Ph COO 2-ClPh O--0 1 d-1 2704 4-MeOPh 4-MeOPh Ph CO CH 2 HO--0 1 d-1 2705 4-MeOPh 4-MeOPh Ph CO CH 2 HS--0 1 d-1 2706 4-MeOPh 4-MeOPh Ph CO PhE HO--0 1 d-1 2707 4-MeOPh 4-MeOPh Ph CO NH Pr O CH 2 CH 2 O 1 1 d-1 2708 4-MeOPh 4-MeOPh Ph COO Me NH (CH 2 ) 3 -1 1 d-1 2709 4-MeOPh Ph Ph COOHO CH 2 CH 2 O 1 1 d-1 2710 4-MeOPh Ph Ph COSHO CH 2 CH 2 O 1 1 d-1 2711 4-MeOPh Ph Ph CO-----0 0 d-1 2712 4-MeOPh Ph Ph COO Me O--0 1 d-1 2713 4-MeOPh Ph Ph COO Me S-- 0 1 d-1 2714 4-MeOPh Ph Ph COO 2-ClPh O--0 1 d-1 2715 4-MeOPh Ph Ph CO CH 2 HO--0 1 d-1 2716 4-MeOPh Ph Ph CO CH 2 HS--0 1 d-1 2717 4-MeOPh Ph Ph CO PhE HO--0 1 d-1 2718 4-MeOPh Ph Ph CO NH Pr O CH 2 CH 2 O 1 1 d-1 2719 4-MeOPh Ph Ph COO Me NH (CH 2 ) 3 -1 1 d-1 2720 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 d-1 2721 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 d-1 2722 tBu Ph Ph Si O-----0 0 d-1 2723 tBu Ph Ph Si OO Me O--0 1 d-1 2724 tBu Ph Ph Si OO Me S--0 1 d -1 2725 tBu Ph Ph Si OO 2-ClPh O--0 1 d-1 2726 tBu Ph Ph Si O CH 2 HO--0 1 d-1 2727 tBu Ph Ph Si O CH 2 HS--0 1 d-1 2728 tBu Ph Ph Si O PhE HO--0 1 d-1 2729 tBu Ph Ph Si O NH Pr O CH 2 CH 2 O 1 1 d-1 2730 tBu Ph Ph Si OO Me NH (CH 2 ) 3 -1 1 d-1 2731 Ph Ph Ph CSOHO CH 2 CH 2 O 1 1 d-1 2732 Ph Ph Ph CSSHO CH 2 CH 2 O 1 1 d-1 2733 Ph Ph Ph CS-----0 0 d-1 2734 Ph Ph Ph CSO Me O--0 1 d-1 2735 Ph Ph Ph CSO Me S--0 1 d-1 2736 Ph Ph Ph CSO 2-ClPh O--0 1 d-1 2737 Ph Ph Ph CS CH 2 HO--0 1 d-1 2738 Ph Ph Ph CS CH 2 HS--0 1 d-1 2739 Ph Ph Ph CS PhE HO--0 1 d-1 2740 Ph Ph Ph CS NH Pr O CH 2 CH 2 O 1 1 d-1 2741 Ph Ph Ph CSO Me NH (CH 2 ) 3 -1 1 d-1 2742 4-BnOPh HHCOOHO CH 2 CH 2 O 1 1 d-1 2743 4-BnOPh HHCOSHO CH 2 CH 2 O 1 1 d-1 2744 4-BnOPh HHCO-----0 0 d-1 2745 4-BnOPh HHCOO Me O--0 1 d-1 2746 4-BnOPh HHCOO Me S--0 1 d-1 2747 4-BnOPh HHCOO 2-ClPh O--0 1 d-1 2748 4-BnOPh HHCO CH 2 HO--0 1 d-1 2749 4-BnOPh HHCO CH 2 HS--0 1 d-1 2750 4-BnOPh HHCO PhE HO--0 1 d-1 2751 4-BnOPh HHCO NH Pr O CH 2 CH 2 O 1 1 d-1 2752 4-BnOPh HHCOO Me NH (CH 2 ) 3 -1 1 d-1 2753 Ph Xanthen-9-yl OOHO CH 2 CH 2 O 1 1 d-1 2754 Ph Xanthen-9-yl OSHO CH 2 CH 2 O 1 1 d-1 2755 Ph Xanthen-9-yl O-----0 0 d-1 2756 Ph Xanthen-9-yl OO Me O--0 1 d-1 2757 Ph Xanthen-9-yl OO Me S--0 1 d-1 2758 Ph Xanthen-9-yl OO 2-ClPh O--0 1 d-1 2759 Ph Xanthen-9-yl O CH 2 HO--0 1 d-1 2760 Ph Xanthen-9-yl O CH 2 HS--0 1 d-1 2761 Ph Xanthen-9-yl O PhE HO--0 1 d-1 2762 Ph Xanthen-9-yl O NH Pr O CH 2 CH 2 O 1 1 d-1 2763 Ph Xanthen-9-yl OO Me NH (CH 2 ) 3 -1 1 d-1 2764 Ph Fluoren-9-yl OOHO CH 2 CH 2 O 1 1 d-1 2765 Ph Fluoren-9-yl OSHO CH 2 CH 2 O 1 1 d-1 2766 Ph Fluoren-9-yl O-----0 0 d-1 2767 Ph Fluoren-9-yl OO Me O--0 1 d-1 2768 Ph Fluoren-9-yl OO Me S--0 1 d-1 2769 Ph Fluoren-9-yl OO 2-ClPh O--0 1 d-1 2770 Ph Fluoren-9-yl O CH 2 HO--0 1 d-1 2771 Ph Fluoren-9-yl O CH 2 HS--0 1 d-1 2772 Ph Fluoren-9-yl O PhE HO--0 1 d-1 2773 Ph Fluoren-9-yl O NH Pr O CH 2 CH 2 O 1 1 d-1 2774 Ph Fluoren-9-yl OO Me NH (CH 2 ) 3 -1 1 d-1 2775 3,4-DBP HHCSOHO CH 2 CH 2 O 1 1 1-1 2776 3,4-DBP HHCSSHO CH 2 CH 2 O 1 1 1-1 2777 3,4-DBP HHCS-----0 0 1-1 2778 3,4-DBP HHCSO Me O--0 1 1-1 2779 3,4-DBP HHCSO Me S-- 0 1 1-1 2780 3,4-DBP HHCSO 2-ClPh O--0 1 1-1 2781 3,4-DBP HHCS CH 2 HO--0 1 1-1 2782 3,4-DBP HHCS CH 2 HS--0 1 1-1 2783 3,4-DBP HHCS PhE HO--0 1 1-1 2784 3,4-DBP HHCS NH Pr O CH 2 CH 2 O 1 1 1-1 2785 3,4-DBP HHCSO Me NH (CH 2 ) 3 -1 1 1-1 2786 9-ANT HHCSOHO CH 2 CH 2 O 1 1 1-1 2787 9-ANT HHCSSHO CH 2 CH 2 O 1 1 1-1 2788 9-ANT HHCS-----0 0 1-1 2789 9-ANT HHCSO Me O--0 1 1-1 2790 9-ANT HHCSO Me S--0 1 1-1 2791 9-ANT HHCSO 2-ClPh O--0 1 1-1 2792 9-ANT HHCS CH 2 HO--0 1 1-1 2793 9-ANT HHCS CH 2 HS--0 1 1-1 2794 9-ANT HHCS PhE HO--0 1 1-1 2795 9-ANT HHCS NH Pr O CH 2 CH 2 O 1 1 1-1 2796 9-ANT HHCSO Me NH (CH 2 ) 3 -1 1 1-1 2797 2-NAP HHCSOHO CH 2 CH 2 O 1 1 1-1 2798 2-NAP HHCSSHO CH 2 CH 2 O 1 1 1-1 2799 2-NAP HHCS-----0 0 1-1 2800 2-NAP HHCSO Me O--0 1 1-1 2801 2-NAP HHCSO Me S--0 1 1-1 2802 2-NAP HHCSO 2-ClPh O--0 1 1-1 2803 2-NAP HHCS CH 2 HO--0 1 1-1 2804 2-NAP HHCS CH 2 HS--0 1 1-1 2805 2-NAP HHCS PhE HO--0 1 1-1 2806 2-NAP HHCS NH Pr O CH 2 CH 2 O 1 1 1-1 2807 2-NAP HHCSO Me NH (CH 2 ) 3 -1 1 1-1 2808 BDBBP HHCSOHO CH 2 CH 2 O 1 1 1-1 2809 BDBBP HHCSSHO CH 2 CH 2 O 1 1 1-1 2810 BDBBP HHCS-----0 0 1-1 2811 BDBBP HHCSO Me O--0 1 1-1 2812 BDBBP HHCSO Me S--0 1 1-1 2813 BDBBP HHCSO 2-ClPh O --0 1 1-1 2814 BDBBP HHCS CH 2 HO--0 1 1-1 2815 BDBBP HHCS CH 2 HS--0 1 1-1 2816 BDBBP HHCS PhE HO--0 1 1-1 2817 BDBBP HHCS NH Pr O CH 2 CH 2 O 1 1 1-1 2818 BDBBP HHCSO Me NH (CH 2 ) 3 -1 1 1-1 2819 3,4-DBP HHCSOHO CH 2 CH 2 O 1 1 c-1 2820 3,4-DBP HHCSSHO CH 2 CH 2 O 1 1 c-1 2821 3,4-DBP HHCS-----0 0 c-1 2822 3,4-DBP HHCSO Me O--0 1 c-1 2823 3,4-DBP HHCSO Me S-- 0 1 c-1 2824 3,4-DBP HHCSO 2-ClPh O--0 1 c-1 2825 3,4-DBP HHCS CH 2 HO--0 1 c-1 2826 3,4-DBP HHCS CH 2 HS--0 1 c-1 2827 3,4-DBP HHCS PhE HO--0 1 c-1 2828 3,4-DBP HHCS NH Pr O CH 2 CH 2 O 1 1 c-1 2829 3,4-DBP HHCSO Me NH (CH 2 ) 3 -1 1 c-1 2830 9-ANT HHCSOHO CH 2 CH 2 O 1 1 c-1 2831 9-ANT HHCSSHO CH 2 CH 2 O 1 1 c-1 2832 9-ANT HHCS-----0 0 c-1 2833 9-ANT HHCSO Me O--0 1 c-1 2834 9-ANT HHCSO Me S--0 1 c-1 2835 9-ANT HHCSO 2-ClPh O--0 1 c-1 2836 9-ANT HHCS CH 2 HO--0 1 c-1 2837 9-ANT HHCS CH 2 HS--0 1 c-1 2838 9-ANT HHCS PhE HO--0 1 c-1 2839 9-ANT HHCS NH Pr O CH 2 CH 2 O 1 1 c-1 2840 9-ANT HHCSO Me NH (CH 2 ) 3 -1 1 c-1 2841 2-NAP HHCSOHO CH 2 CH 2 O 1 1 c-1 2842 2-NAP HHCSSHO CH 2 CH 2 O 1 1 c-1 2843 2-NAP HHCS-----0 0 c-1 2844 2-NAP HHCSO Me O--0 1 c-1 2845 2-NAP HHCSO Me S--0 1 c-1 2846 2-NAP HHCSO 2-ClPh O--0 1 c-1 2847 2-NAP HHCS CH 2 HO--0 1 c-1 2848 2-NAP HHCS CH 2 HS--0 1 c-1 2849 2-NAP HHCS PhE HO--0 1 c-1 2850 2-NAP HHCS NH Pr O CH 2 CH 2 O 1 1 c-1 2851 2-NAP HHCSO Me NH (CH 2 ) 3 -1 1 c-1 2852 BDBBP HHCSOHO CH 2 CH 2 O 1 1 c-1 2853 BDBBP HHCSSHO CH 2 CH 2 O 1 1 c-1 2854 BDBBP HHCS-----0 0 c-1 2855 BDBBP HHCSO Me O--0 1 c-1 2856 BDBBP HHCSO Me S--0 1 c-1 2857 BDBBP HHCSO 2-ClPh O --0 1 c-1 2858 BDBBP HHCS CH 2 HO--0 1 c-1 2859 BDBBP HHCS CH 2 HS--0 1 c-1 2860 BDBBP HHCS PhE HO--0 1 c-1 2861 BDBBP HHCS NH Pr O CH 2 CH 2 O 1 1 c-1 2862 BDBBP HHCSO Me NH (CH 2 ) 3 -1 1 c-1 2863 3,4-DBP HHCSOHO CH 2 CH 2 O 1 1 d-1 2864 3,4-DBP HHCSSHO CH 2 CH 2 O 1 1 d-1 2865 3,4-DBP HHCS-----0 0 d-1 2866 3,4-DBP HHCSO Me O--0 1 d-1 2867 3,4-DBP HHCSO Me S-- 0 1 d-1 2868 3,4-DBP HHCSO 2-ClPh O--0 1 d-1 2869 3,4-DBP HHCS CH 2 HO--0 1 d-1 2870 3,4-DBP HHCS CH 2 HS--0 1 d-1 2871 3,4-DBP HHCS PhE HO--0 1 d-1 2872 3,4-DBP HHCS NH Pr O CH 2 CH 2 O 1 1 d-1 2873 3,4-DBP HHCSO Me NH (CH 2 ) 3 -1 1 d-1 2874 9-ANT HHCSOHO CH 2 CH 2 O 1 1 d-1 2875 9-ANT HHCSSHO CH 2 CH 2 O 1 1 d-1 2876 9-ANT HHCS-----0 0 d-1 2877 9-ANT HHCSO Me O--0 1 d-1 2878 9-ANT HHCSO Me S--0 1 d-1 2879 9-ANT HHCSO 2-ClPh O--0 1 d-1 2880 9-ANT HHCS CH 2 HO--0 1 d-1 2881 9-ANT HHCS CH 2 HS--0 1 d-1 2882 9-ANT HHCS PhE HO--0 1 d-1 2883 9-ANT HHCS NH Pr O CH 2 CH 2 O 1 1 d-1 2884 9-ANT HHCSO Me NH (CH 2 ) 3 -1 1 d-1 2885 2-NAP HHCSOHO CH 2 CH 2 O 1 1 d-1 2886 2-NAP HHCSSHO CH 2 CH 2 O 1 1 d-1 2887 2-NAP HHCS-----0 0 d-1 2888 2-NAP HHCSO Me O--0 1 d-1 2889 2-NAP HHCSO Me S--0 1 d-1 2890 2-NAP HHCSO 2-ClPh O--0 1 d-1 2891 2-NAP HHCS CH 2 HO--0 1 d-1 2892 2-NAP HHCS CH 2 HS--0 1 d-1 2893 2-NAP HHCS PhE HO--0 1 d-1 2894 2-NAP HHCS NH Pr O CH 2 CH 2 O 1 1 d-1 2895 2-NAP HHCSO Me NH (CH 2 ) 3 -1 1 d-1 2896 BDBBP HHCSOHO CH 2 CH 2 O 1 1 d-1 2897 BDBBP HHCSSHO CH 2 CH 2 O 1 1 d-1 2898 BDBBP HHCS-----0 0 d-1 2899 BDBBP HHCSO Me O--0 1 d-1 2900 BDBBP HHCSO Me S--0 1 d-1 2901 BDBBP HHCSO 2-ClPh O --0 1 d-1 2902 BDBBP HHCS CH 2 HO--0 1 d-1 2903 BDBBP HHCS CH 2 HS--0 1 d-1 2904 BDBBP HHCS PhE HO--0 1 d-1 2905 BDBBP HHCS NH Pr O CH 2 CH 2 O 1 1 d-1 2906 BDBBP HHCSO Me NH (CH 2 ) 3 -1 1 d-1 2907 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 e 2908 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 e 2909 3,4-DBP HHCO-----0 0 e 2910 3,4-DBP HHCOO Me O--0 1 e 2911 3,4-DBP HHCOO Me S--0 1 e 2912 3, 4-DBP HHCOO 2-ClPh O--0 1 e 2913 3,4-DBP HHCO CH 2 HO--0 1 e 2914 3,4-DBP HHCO CH 2 HS--0 1 e 2915 3,4-DBP HHCO PhE HO--0 1 e 2916 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 e 2917 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 e 2918 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 f 2919 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 f 2920 3,4-DBP HHCO-----0 0 f 2921 3,4-DBP HHCOO Me O--0 1 f 2922 3,4-DBP HHCOO Me S--0 1 f 2923 3, 4-DBP HHCOO 2-ClPh O--0 1 f 2924 3,4-DBP HHCO CH 2 HO--0 1 f 2925 3,4-DBP HHCO CH 2 HS--0 1 f 2926 3,4-DBP HHCO PhE HO--0 1 f 2927 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 f 2928 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 f 2929 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 g 2930 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 g 2931 3,4-DBP HHCO-----0 0 g 2932 3,4-DBP HHCOO Me O--0 1 g 2933 3,4-DBP HHCOO Me S--0 1 g 2934 3, 4-DBP HHCOO 2-ClPh O--0 1 g 2935 3,4-DBP HHCO CH 2 HO--0 1 g 2936 3,4-DBP HHCO CH 2 HS--0 1 g 2937 3,4-DBP HHCO PhE HO--0 1 g 2938 3,4-DBP HHCO NH Pr O CH 2 CH 2 O 1 1 g 2939 3,4-DBP HHCOO Me NH (CH 2 ) 3 -1 1 g 2940 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-2 2941 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-2 2942 3,4-DBP HHCO-----0 0 1-2 2943 3,4-DBP HHCOO Me O--0 1 1-2 2944 3,4-DBP HHCOO Me S-- 0 1 1-2 2945 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-2 2946 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-2 2947 Ph Ph Ph CO-----0 0 1-2 2948 Ph Ph Ph COO Me O--0 1 1-2 2949 Ph Ph Ph COO Me S--0 1 1-2 2950 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-2 2951 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-2 2952 3,5-DBP HHCO-----0 0 1-2 2953 3,5-DBP HHCOO Me O--0 1 1-2 2954 3,5-DBP HHCOO Me S-- 0 1 1-2 2955 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-2 2956 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-2 2957 tBu Ph Ph Si O-----0 0 1-2 2958 tBu Ph Ph Si OO Me O--0 1 1-2 2959 tBu Ph Ph Si OO Me S--0 1 1 -2 2960 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-3 2961 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-3 2962 3,4-DBP HHCO-----0 0 1-3 2963 3,4-DBP HHCOO Me O--0 1 1-3 2964 3,4-DBP HHCOO Me S-- 0 1 1-3 2965 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-3 2966 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-3 2967 Ph Ph Ph CO-----0 0 1-3 2968 Ph Ph Ph COO Me O--0 1 1-3 2969 Ph Ph Ph COO Me S--0 1 1-3 2970 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-3 2971 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-3 2972 3,5-DBP HHCO-----0 0 1-3 2973 3,5-DBP HHCOO Me O--0 1 1-3 2974 3,5-DBP HHCOO Me S-- 0 1 1-3 2975 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-3 2976 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-3 2977 tBu Ph Ph Si O-----0 0 1-3 2978 tBu Ph Ph Si OO Me O--0 1 1-3 2979 tBu Ph Ph Si OO Me S--0 1 1 -3 2980 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-4 2981 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-4 2982 3,4-DBP HHCO-----0 0 1-4 2983 3,4-DBP HHCOO Me O--0 1 1-4 2984 3,4-DBP HHCOO Me S-- 0 1 1-4 2985 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-4 2986 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-4 2987 Ph Ph Ph CO-----0 0 1-4 2988 Ph Ph Ph COO Me O--0 1 1-4 2989 Ph Ph Ph COO Me S--0 1 1-4 2990 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-4 2991 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-4 2992 3,5-DBP HHCO-----0 0 1-4 2993 3,5-DBP HHCOO Me O--0 1 1-4 2994 3,5-DBP HHCOO Me S-- 0 1 1-4 2995 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-4 2996 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-4 2997 tBu Ph Ph Si O-----0 0 1-4 2998 tBu Ph Ph Si OO Me O--0 1 1-4 2999 tBu Ph Ph Si OO Me S--0 1 1 -4 3000 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-5 3001 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-5 3002 3,4-DBP HHCO-----0 0 1-5 3003 3,4-DBP HHCOO Me O--0 1 1-5 3004 3,4-DBP HHCOO Me S-- 0 1 1-5 3005 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-5 3006 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-5 3007 Ph Ph Ph CO-----0 0 1-5 3008 Ph Ph Ph COO Me O--0 1 1-5 3009 Ph Ph COO Me S--0 1 1-5 3010 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-5 3011 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-5 3012 3,5-DBP HHCO-----0 0 1-5 3013 3,5-DBP HHCOO Me O--0 1 1-5 3014 3,5-DBP HHCOO Me S-- 0 1 1-5 3015 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-5 3016 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-5 3017 tBu Ph Ph Si O-----0 0 1-5 3018 tBu Ph Ph Si OO Me O--0 1 1-5 3019 tBu Ph Ph Si OO Me S--0 1 1 -5 3020 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-6 3021 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-6 3022 3,4-DBP HHCO-----0 0 1-6 3023 3,4-DBP HHCOO Me O--0 1 1-6 3024 3,4-DBP HHCOO Me S-- 0 1 1-6 3025 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-6 3026 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-6 3027 Ph Ph Ph CO-----0 0 1-6 3028 Ph Ph Ph COO Me O--0 1 1-6 3029 Ph Ph Ph COO Me S--0 1 1-6 3030 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-6 3031 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-6 3032 3,5-DBP HHCO-----0 0 1-6 3033 3,5-DBP HHCOO Me O--0 1 1-6 3034 3,5-DBP HHCOO Me S-- 0 1 1-6 3035 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-6 3036 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-6 3037 tBu Ph Ph Si O-----0 0 1-6 3038 tBu Ph Ph Si OO Me O--0 1 1-6 3039 tBu Ph Ph Si OO Me S--0 1 1 -6 3040 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-7 3041 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-7 3042 3,4-DBP HHCO-----0 0 1-7 3043 3,4-DBP HHCOO Me O--0 1 1-7 3044 3,4-DBP HHCOO Me S-- 0 1 1-7 3045 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-7 3046 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-7 3047 Ph Ph Ph CO-----0 0 1-7 3048 Ph Ph Ph COO Me O--0 1 1-7 3049 Ph Ph Ph COO Me S--0 1 1-7 3050 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-7 3051 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-7 3052 3,5-DBP HHCO-----0 0 1-7 3053 3,5-DBP HHCOO Me O--0 1 1-7 3054 3,5-DBP HHCOO Me S-- 0 1 1-7 3055 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-7 3056 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-7 3057 tBu Ph Ph Si O-----0 0 1-7 3058 tBu Ph Ph Si OO Me O--0 1 1-7 3059 tBu Ph Ph Si OO Me S--0 1 1 -7 3060 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-8 3061 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-8 3062 3,4-DBP HHCO-----0 0 1-8 3063 3,4-DBP HHCOO Me O--0 1 1-8 3064 3,4-DBP HHCOO Me S-- 0 1 1-8 3065 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-8 3066 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-8 3067 Ph Ph Ph CO-----0 0 1-8 3068 Ph Ph Ph COO Me O--0 1 1-8 3069 Ph Ph Ph COO Me S--0 1 1-8 3070 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-8 3071 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-8 3072 3,5-DBP HHCO-----0 0 1-8 3073 3,5-DBP HHCOO Me O--0 1 1-8 3074 3,5-DBP HHCOO Me S-- 0 1 1-8 3075 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-8 3076 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-8 3077 tBu Ph Ph Si O-----0 0 1-8 3078 tBu Ph Ph Si OO Me O--0 1 1-8 3079 tBu Ph Ph Si OO Me S--0 1 1 -8 3080 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-9 3081 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-9 3082 3,4-DBP HHCO-----0 0 1-9 3083 3,4-DBP HHCOO Me O--0 1 1-9 3084 3,4-DBP HHCOO Me S-- 0 1 1-9 3085 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-9 3086 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-9 3087 Ph Ph Ph CO-----0 0 1-9 3088 Ph Ph Ph COO Me O--0 1 1-9 3089 Ph Ph Ph COO Me S--0 1 1-9 3090 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-9 3091 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-9 3092 3,5-DBP HHCO-----0 0 1-9 3093 3,5-DBP HHCOO Me O--0 1 1-9 3094 3,5-DBP HHCOO Me S-- 0 1 1-9 3095 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-9 3096 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-9 3097 tBu Ph Ph Si O-----0 0 1-9 3098 tBu Ph Ph Si OO Me O--0 1 1-9 3099 tBu Ph Ph Si OO Me S--0 1 1 -9 3100 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-10 3101 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-10 3102 3,4-DBP HHCO-----0 0 1-10 3103 3,4-DBP HHCOO Me O--0 1 1-10 3104 3,4-DBP HHCOO Me S-- 0 1 1-10 3105 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-10 3106 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-10 3107 Ph Ph Ph CO-----0 0 1-10 3108 Ph Ph Ph COO Me O--0 1 1-10 3109 Ph Ph COO Me S--0 1 1-10 3110 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-10 3111 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-10 3112 3,5-DBP HHCO-----0 0 1-10 3113 3,5-DBP HHCOO Me O--0 1 1-10 3114 3,5-DBP HHCOO Me S-- 0 1 1-10 3115 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-10 3116 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-10 3117 tBu Ph Ph Si O-----0 0 1-10 3118 tBu Ph Ph Si OO Me O--0 1 1-10 3119 tBu Ph Ph Si OO Me S--0 1 1 -10 3120 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-11 3121 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-11 3122 3,4-DBP HHCO-----0 0 1-11 3123 3,4-DBP HHCOO Me O--0 1 1-11 3124 3,4-DBP HHCOO Me S-- 0 1 1-11 3125 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-11 3126 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-11 3127 Ph Ph Ph CO-----0 0 1-11 3128 Ph Ph Ph COO Me O--0 1 1-11 3129 Ph Ph Ph COO Me S--0 1 1-11 3130 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-11 3131 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-11 3132 3,5-DBP HHCO-----0 0 1-11 3133 3,5-DBP HHCOO Me O--0 1 1-11 3134 3,5-DBP HHCOO Me S-- 0 1 1-11 3135 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-11 3136 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-11 3137 tBu Ph Ph Si O-----0 0 1-11 3138 tBu Ph Ph Si OO Me O--0 1 1-11 3139 tBu Ph Ph Si OO Me S--0 1 1 -11 3140 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-12 3141 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-12 3142 3,4-DBP HHCO-----0 0 1-12 3143 3,4-DBP HHCOO Me O--0 1 1-12 3144 3,4-DBP HHCOO Me S-- 0 1 1-12 3145 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-12 3146 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-12 3147 Ph Ph Ph CO-----0 0 1-12 3148 Ph Ph Ph COO Me O--0 1 1-12 3149 Ph Ph Ph COO Me S--0 1 1-12 3150 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-12 3151 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-12 3152 3,5-DBP HHCO-----0 0 1-12 3153 3,5-DBP HHCOO Me O--0 1 1-12 3154 3,5-DBP HHCOO Me S-- 0 1 1-12 3155 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-12 3156 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-12 3157 tBu Ph Ph Si O-----0 0 1-12 3158 tBu Ph Ph Si OO Me O--0 1 1-12 3159 tBu Ph Ph Si OO Me S--0 1 1 -12 3160 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-13 3161 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-13 3162 3,4-DBP HHCO-----0 0 1-13 3163 3,4-DBP HHCOO Me O--0 1 1-13 3164 3,4-DBP HHCOO Me S-- 0 1 1-13 3165 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-13 3166 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-13 3167 Ph Ph Ph CO-----0 0 1-13 3168 Ph Ph Ph COO Me O--0 1 1-13 3169 Ph Ph Ph COO Me S--0 1 1-13 3170 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-13 3171 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-13 3172 3,5-DBP HHCO-----0 0 1-13 3173 3,5-DBP HHCOO Me O--0 1 1-13 3174 3,5-DBP HHCOO Me S-- 0 1 1-13 3175 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-13 3176 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-13 3177 tBu Ph Ph Si O-----0 0 1-13 3178 tBu Ph Ph Si OO Me O--0 1 1-13 3179 tBu Ph Ph Si OO Me S--0 1 1 -13 3180 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-14 3181 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-14 3182 3,4-DBP HHCO-----0 0 1-14 3183 3,4-DBP HHCOO Me O--0 1 1-14 3184 3,4-DBP HHCOO Me S-- 0 1 1-14 3185 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-14 3186 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-14 3187 Ph Ph Ph CO-----0 0 1-14 3188 Ph Ph Ph COO Me O--0 1 1-14 3189 Ph Ph Ph COO Me S--0 1 1-14 3190 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-14 3191 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-14 3192 3,5-DBP HHCO-----0 0 1-14 3193 3,5-DBP HHCOO Me O--0 1 1-14 3194 3,5-DBP HHCOO Me S-- 0 1 1-14 3195 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-14 3196 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-14 3197 tBu Ph Ph Si O-----0 0 1-14 3198 tBu Ph Ph Si OO Me O--0 1 1-14 3199 tBu Ph Ph Si OO Me S--0 1 1 -14 3200 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 1-15 3201 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 1-15 3202 3,4-DBP HHCO-----0 0 1-15 3203 3,4-DBP HHCOO Me O--0 1 1-15 3204 3,4-DBP HHCOO Me S-- 0 1 1-15 3205 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 1-15 3206 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 1-15 3207 Ph Ph Ph CO-----0 0 1-15 3208 Ph Ph Ph COO Me O--0 1 1-15 3209 Ph Ph Ph COO Me S--0 1 1-15 3210 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 1-15 3211 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 1-15 3212 3,5-DBP HHCO-----0 0 1-15 3213 3,5-DBP HHCOO Me O--0 1 1-15 3214 3,5-DBP HHCOO Me S-- 0 1 1-15 3215 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 1-15 3216 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 1-15 3217 tBu Ph Ph Si O-----0 0 1-15 3218 tBu Ph Ph Si OO Me O--0 1 1-15 3219 tBu Ph Ph Si OO Me S--0 1 1 -15 3220 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 3-2 3221 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 3-2 3222 3,4-DBP HHCO-----0 0 3-2 3223 3,4-DBP HHCOO Me O--0 1 3-2 3224 3,4-DBP HHCOO Me S-- 0 1 3-2 3225 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 3-2 3226 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 3-2 3227 Ph Ph Ph CO-----0 0 3-2 3228 Ph Ph Ph COO Me O--0 1 3-2 3229 Ph Ph Ph COO Me S--0 1 3-2 3230 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 3-2 3231 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 3-2 3232 3,5-DBP HHCO-----0 0 3-2 3233 3,5-DBP HHCOO Me O--0 1 3-2 3234 3,5-DBP HHCOO Me S-- 0 1 3-2 3235 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 3-2 3236 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 3-2 3237 tBu Ph Ph Si O-----0 0 3-2 3238 tBu Ph Ph Si OO Me O--0 1 3-2 3239 tBu Ph Ph Si OO Me S--0 1 3 -2 3240 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 3-3 3241 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 3-3 3242 3,4-DBP HHCO-----0 0 3-3 3243 3,4-DBP HHCOO Me O--0 1 3-3 3244 3,4-DBP HHCOO Me S-- 0 1 3-3 3245 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 3-3 3246 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 3-3 3247 Ph Ph Ph CO-----0 0 3-3 3248 Ph Ph Ph COO Me O--0 1 3-3 3249 Ph Ph Ph COO Me S--0 1 3-3 3250 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 3-3 3251 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 3-3 3252 3,5-DBP HHCO-----0 0 3-3 3253 3,5-DBP HHCOO Me O--0 1 3-3 3254 3,5-DBP HHCOO Me S-- 0 1 3-3 3255 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 3-3 3256 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 3-3 3257 tBu Ph Ph Si O-----0 0 3-3 3258 tBu Ph Ph Si OO Me O--0 1 3-3 3259 tBu Ph Ph Si OO Me S--0 1 3 -3 3260 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 a-2 3261 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 a-2 3262 3,4-DBP HHCO-----0 0 a-2 3263 3,4-DBP HHCOO Me O--0 1 a-2 3264 3,4-DBP HHCOO Me S-- 0 1 a-2 3265 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 a-2 3266 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 a-2 3267 Ph Ph Ph CO-----0 0 a-2 3268 Ph Ph Ph COO Me O--0 1 a-2 3269 Ph Ph Ph COO Me S--0 1 a-2 3270 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 a-2 3271 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 a-2 3272 3,5-DBP HHCO-----0 0 a-2 3273 3,5-DBP HHCOO Me O--0 1 a-2 3274 3,5-DBP HHCOO Me S-- 0 1 a-2 3275 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 a-2 3276 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 a-2 3277 tBu Ph Ph Si O-----0 0 a-2 3278 tBu Ph Ph Si OO Me O--0 1 a-2 3279 tBu Ph Ph Si OO Me S--0 1 a -2 3280 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 a-3 3281 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 a-3 3282 3,4-DBP HHCO-----0 0 a-3 3283 3,4-DBP HHCOO Me O--0 1 a-3 3284 3,4-DBP HHCOO Me S-- 0 1 a-3 3285 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 a-3 3286 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 a-3 3287 Ph Ph Ph CO-----0 0 a-3 3288 Ph Ph Ph COO Me O--0 1 a-3 3289 Ph Ph COO Me S--0 1 a-3 3290 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 a-3 3291 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 a-3 3292 3,5-DBP HHCO-----0 0 a-3 3293 3,5-DBP HHCOO Me O--0 1 a-3 3294 3,5-DBP HHCOO Me S-- 0 1 a-3 3295 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 a-3 3296 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 a-3 3297 tBu Ph Ph Si O-----0 0 a-3 3298 tBu Ph Ph Si OO Me O--0 1 a-3 3299 tBu Ph Ph Si OO Me S--0 1 a -3 3300 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 b-2 3301 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 b-2 3302 3,4-DBP HHCO-----0 0 b-2 3303 3,4-DBP HHCOO Me O--0 1 b-2 3304 3,4-DBP HHCOO Me S-- 0 1 b-2 3305 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 b-2 3306 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 b-2 3307 Ph Ph Ph CO-----0 0 b-2 3308 Ph Ph Ph COO Me O--0 1 b-2 3309 Ph Ph Ph COO Me S--0 1 b-2 3310 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 b-2 3311 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 b-2 3312 3,5-DBP HHCO-----0 0 b-2 3313 3,5-DBP HHCOO Me O--0 1 b-2 3314 3,5-DBP HHCOO Me S-- 0 1 b-2 3315 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 b-2 3316 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 b-2 3317 tBu Ph Ph Si O-----0 0 b-2 3318 tBu Ph Ph Si OO Me O--0 1 b-2 3319 tBu Ph Ph Si OO Me S--0 1 b -2 3320 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 b-3 3321 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 b-3 3322 3,4-DBP HHCO-----0 0 b-3 3323 3,4-DBP HHCOO Me O--0 1 b-3 3324 3,4-DBP HHCOO Me S-- 0 1 b-3 3325 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 b-3 3326 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 b-3 3327 Ph Ph Ph CO-----0 0 b-3 3328 Ph Ph Ph COO Me O--0 1 b-3 3329 Ph Ph Ph COO Me S--0 1 b-3 3330 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 b-3 3331 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 b-3 3332 3,5-DBP HHCO-----0 0 b-3 3333 3,5-DBP HHCOO Me O--0 1 b-3 3334 3,5-DBP HHCOO Me S-- 0 1 b-3 3335 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 b-3 3336 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 b-3 3337 tBu Ph Ph Si O-----0 0 b-3 3338 tBu Ph Ph Si OO Me O--0 1 b-3 3339 tBu Ph Ph Si OO Me S--0 1 b -3 3340 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 c-2 3341 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 c-2 3342 3,4-DBP HHCO-----0 0 c-2 3343 3,4-DBP HHCOO Me O--0 1 c-2 3344 3,4-DBP HHCOO Me S-- 0 1 c-2 3345 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 c-2 3346 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 c-2 3347 Ph Ph Ph CO-----0 0 c-2 3348 Ph Ph Ph COO Me O--0 1 c-2 3349 Ph Ph Ph COO Me S--0 1 c-2 3350 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 c-2 3351 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 c-2 3352 3,5-DBP HHCO-----0 0 c-2 3353 3,5-DBP HHCOO Me O--0 1 c-2 3354 3,5-DBP HHCOO Me S-- 0 1 c-2 3355 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 c-2 3356 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 c-2 3357 tBu Ph Ph Si O-----0 0 c-2 3358 tBu Ph Ph Si OO Me O--0 1 c-2 3359 tBu Ph Ph Si OO Me S--0 1 c -2 3360 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 c-3 3361 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 c-3 3362 3,4-DBP HHCO-----0 0 c-3 3363 3,4-DBP HHCOO Me O--0 1 c-3 3364 3,4-DBP HHCOO Me S-- 0 1 c-3 3365 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 c-3 3366 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 c-3 3367 Ph Ph Ph CO-----0 0 c-3 3368 Ph Ph Ph COO Me O--0 1 c-3 3369 Ph Ph Ph COO Me S--0 1 c-3 3370 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 c-3 3371 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 c-3 3372 3,5-DBP HHCO-----0 0 c-3 3373 3,5-DBP HHCOO Me O--0 1 c-3 3374 3,5-DBP HHCOO Me S-- 0 1 c-3 3375 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 c-3 3376 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 c-3 3377 tBu Ph Ph Si O-----0 0 c-3 3378 tBu Ph Ph Si OO Me O--0 1 c-3 3379 tBu Ph Ph Si OO Me S--0 1 c -3 3380 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 d-2 3381 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 d-2 3382 3,4-DBP HHCO-----0 0 d-2 3383 3,4-DBP HHCOO Me O--0 1 d-2 3384 3,4-DBP HHCOO Me S-- 0 1 d-2 3385 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 d-2 3386 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 d-2 3387 Ph Ph Ph CO-----0 0 d-2 3388 Ph Ph Ph COO Me O--0 1 d-2 3389 Ph Ph Ph COO Me S--0 1 d-2 3390 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 d-2 3391 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 d-2 3392 3,5-DBP HHCO-----0 0 d-2 3393 3,5-DBP HHCOO Me O--0 1 d-2 3394 3,5-DBP HHCOO Me S-- 0 1 d-2 3395 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 d-2 3396 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 d-2 3397 tBu Ph Ph Si O-----0 0 d-2 3398 tBu Ph Ph Si OO Me O--0 1 d-2 3399 tBu Ph Ph Si OO Me S--0 1 d -2 3400 3,4-DBP HHCOOHO CH 2 CH 2 O 1 1 d-3 3401 3,4-DBP HHCOSHO CH 2 CH 2 O 1 1 d-3 3402 3,4-DBP HHCO-----0 0 d-3 3403 3,4-DBP HHCOO Me O--0 1 d-3 3404 3,4-DBP HHCOO Me S-- 0 1 d-3 3405 Ph Ph Ph COOHO CH 2 CH 2 O 1 1 d-3 3406 Ph Ph Ph COSHO CH 2 CH 2 O 1 1 d-3 3407 Ph Ph Ph CO-----0 0 d-3 3408 Ph Ph Ph COO Me O--0 1 d-3 3409 Ph Ph Ph COO Me S--0 1 d-3 3410 3,5-DBP HHCOOHO CH 2 CH 2 O 1 1 d-3 3411 3,5-DBP HHCOSHO CH 2 CH 2 O 1 1 d-3 3412 3,5-DBP HHCO-----0 0 d-3 3413 3,5-DBP HHCOO Me O--0 1 d-3 3414 3,5-DBP HHCOO Me S-- 0 1 d-3 3415 tBu Ph Ph Si OOHO CH 2 CH 2 O 1 1 d-3 3416 tBu Ph Ph Si OSHO CH 2 CH 2 O 1 1 d-3 3417 tBu Ph Ph Si O-----0 0 d-3 3418 tBu Ph Ph Si OO Me O--0 1 d-3 3419 tBu Ph Ph Si OO Me S--0 1 d -3 ──────────────────────────────────── Among the above-exemplified compounds, preferred compounds include: From 1
Up to 440, 454, 476, 586, 696, 80
6, 916, 1026, 1136, 1246, 135
6, 1466, 1576, 1686, 1763, 177
3, 1793, 1979, 1980, 1990 to 19
94 to 2250, 2326 to 2906, 29
40,2941,942,2960,2961,29
62, 3000, 3001, 3002, 3020, 30
21, 3022, 3060, 3061, 3062, 30
80, 3081, 3082, 3100, 3101, 31
02, 3120, 3121, 3122, 3140, 31
41, 3142, 3160, 3161, 3162, 31
80, 3181, 3182, 3200, 3201, 32
02, 3220, 3221, 3222, 3240, 32
41, 3242, 3260, 3261, 3262, 32
80, 3281, 3282, 3300, 3301, 33
02, 3321, 3322, 3323, 3340, 33
41, 3342, 3360, 3361, 3362, 33
80, 3381, 3382, 3400, 3401, 34
02 compounds can be mentioned.
【００４１】更に、好適な化合物としては、１から１１
０まで、１１３、２２１から３３０まで、３３３、４５
４、１７６３、１７７３、１７９３、１９７９、１９８
０、１９９０から１９９４まで、２２５０、２３３４か
ら２９０６まで、２９４０，２９４１，２９４２，２９
６０，２９６１，２９６２，３０００，３００１，３０
０２，３０２０，３０２１，３０２２，３０６０，３０
６１，３０６２，３０８０，３０８１，３０８２，３１
００，３１０１，３１０２，３１２０，３１２１，３１
２２，３１４０，３１４１，３１４２，３１６０，３１
６１，３１６２，３１８０，３１８１，３１８２，３２
００，３２０１，３２０２，３２２０，３２２１，３２
２２，３２４０，３２４１，３２４２，３２６０，３２
６１，３２６２，３２８０，３２８１，３２８２，３３
００，３３０１，３３０２，３３２１，３３２２，３３
２３，３３４０，３３４１，３３４２，３３６０，３３
６１，３３６２，３３８０，３３８１，３３８２，３４
００，３４０１，３４０２の化合物をあげることができ
る。Further, preferred compounds include 1 to 11
0, 113, 221-330, 333, 45
4, 1763, 1773, 1793, 1979, 198.
0, 1990 to 1994, 2250, 2334 to 2906, 2940, 2994, 1942, 29
60,2961,2962,3000,3001,30
02, 3020, 3021, 3022, 3060, 30
61, 3062, 3080, 3081, 3082, 31
00, 3101, 3102, 3120, 3121, 31
22, 3140, 3141, 3142, 3160, 31
61, 3162, 3180, 3181, 3182, 32
00, 3201, 3202, 3220, 3221, 32
22, 3240, 3241, 3242, 3260, 32
61, 3262, 3280, 3281, 3282, 33
00, 3301, 3302, 3321, 3322, 33
23, 3340, 3341, 3342, 3360, 33
61, 3362, 3380, 3381, 3382, 34
The compounds of 00,3401,3402 can be mentioned.
【００４２】最も、好適な化合物としては、１、２、
３、４、１２、１３、１４、１５、２５５５、２５５
６、２５５７、２５５８、２５６６、２５６７、２５６
８、２５６９、２６６５、２６６６、２６６７、２６６
８、２６７６、２６７７、２６７８、２６７９をあげる
ことができる。本発明の前記一般式（１）を有する化合
物は、塩の形で使用することができる。そのような塩と
しては、例えばナトリウム、カリウムのようなアルカリ
金属；カルシウムのようなアルカリ土類金属；アンモニ
ア；リジン、アルギニンのような塩基性アミノ酸；トリ
エチルアミンのようなアルキルアミン類；などの無機塩
又は有機塩を挙げることができ、好適にはナトリウム、
カリウムのようなアルカリ金属塩である。Most preferred compounds are 1, 2,
3, 4, 12, 13, 14, 15, 2555, 255
6, 2557, 2558, 2566, 2567, 256
8, 2569, 2665, 2666, 2667, 266
8, 2676, 2677, 2678, 2679 can be mentioned. The compound having the above general formula (1) of the present invention can be used in the form of a salt. Examples of such salts include inorganic salts such as alkali metals such as sodium and potassium; alkaline earth metals such as calcium; ammonia; basic amino acids such as lysine and arginine; alkylamines such as triethylamine; Or an organic salt can be mentioned, preferably sodium,
It is an alkali metal salt such as potassium.
【００４３】[0043]
【化７】 [Chemical 7]
【００４４】[0044]
【化８】 Embedded image
【００４５】[0045]
【化９】 [Chemical 9]
【００４６】[0046]
【化１０】 [Chemical 10]
【００４７】[0047]
【化１１】 [Chemical 11]
【００４８】[0048]
【化１２】 [Chemical 12]
【００４９】[0049]
【化１３】 [Chemical 13]
【００５０】[0050]
【化１４】 Embedded image
【００５１】[0051]
【化１５】 [Chemical 15]
【００５２】[0052]
【発明の実施の形態】本発明の一般式（１）の化合物
は、Ａ−１及びＡ−２法により製造される下記化合物
（２）BEST MODE FOR CARRYING OUT THE INVENTION The compound of the general formula (1) of the present invention is the following compound (2) produced by the methods A-1 and A-2.
【００５３】[0053]
【化１６】 [Chemical 16]
【００５４】及びＢ−１、Ｂ−２、Ｂ−３、Ｂ−４及び
Ｂ−５により製造される下記化合物（３）、（４ａ）、
（４ｂ）、（５）、（６ａ）、（６ｂ）、（６ｃ）、
（６ｄ）、（７ａ）及び（７ｂ）And the following compounds (3), (4a) produced by B-1, B-2, B-3, B-4 and B-5:
(4b), (5), (6a), (6b), (6c),
(6d), (7a) and (7b)
【００５５】[0055]
【化１７】 ＤＭＴ−Ｏ−Ｆ−Ｗ1 （３） ＤＭＴ−Ｏ−Ｆ−Ｗ4b （６ｂ） ＤＭＴ−Ｏ−Ｆ−Ｗ2a （４ａ） ＤＭＴ−Ｏ−Ｆ−Ｗ4c （６ｃ） ＤＭＴ−Ｏ−Ｆ−Ｗ2b （４ｂ） ＤＭＴ−Ｏ−Ｆ−Ｗ4d （６ｄ） ＤＭＴ−Ｏ−Ｆ−Ｗ3 （５） ＤＭＴ−Ｏ−Ｆ−Ｗ5a （７ａ） ＤＭＴ−Ｏ−Ｆ−Ｗ4a （６ａ） ＤＭＴ−Ｏ−Ｆ−Ｗ5b （７ｂ）。Embedded image DMT-O-F-W 1 (3) DMT-O-F-W 4b (6b) DMT-O-F-W 2a (4a) DMT-O-F-W 4c (6c) DMT- OF-W 2b (4b) DMT-O-F-W 4d (6d) DMT-O-F-W 3 (5) DMT-O-F-W 5a (7a) DMT-O-F-W 4a (6a) DMT-O-F- W5b (7b).
【００５６】を原料として用い、Ｃ−１、Ｃ−２及びＣ
−３法で示す方法によって、化合物（２）と上記化合物
（３）、（４ａ）、（４ｂ）、（５）、（６ａ）、（６
ｂ）、（６ｃ）、（６ｄ）、（７ａ）及び（７ｂ）を結
合して、製造することができる。Using as a raw material, C-1, C-2 and C
Compound-3 and the compounds (3), (4a), (4b), (5), (6a) and (6
b), (6c), (6d), (7a) and (7b) can be combined to produce.
【００５７】化合物（２）中、Ｒ1 、Ｒ2 、Ｒ3 、Ｙ
1 、Ｚは、一般式（１）の前述のものと同意義を示し、
Ｄ’は下記のβ群から選択される塩基又は保護された相
同の塩基を示し、前記の有効な塩基配列の５’末端部分
の塩基（以下、５’末端塩基という）と同一である。In the compound (2), R 1 , R 2 , R 3 , Y
1 and Z have the same meanings as described above in the general formula (1),
D ′ represents a base selected from the following β group or a protected homologous base, which is the same as the base at the 5′-terminal portion of the effective base sequence (hereinafter referred to as the 5′-terminal base).
【００５８】［Ｆ群］ アデニン、グアニン、シトシン、チミン及び５−メチル
シトシン Ｂ−１法は前記有効な塩基配列の３’末端部分のＤＮＡ
合成のための保護基を有するヌクレオシド（以下３’末
端ヌクレオシドという）を結合させたＤＮＡ合成機で使
用されるリンカーを有するコントロールド・ポア・グラ
ス（以下ＣＰＧという）とＤＮＡ合成機用に市販されて
いるヌクレオシドホスホロアミダイト試薬、ヌクレオシ
ドメチルホスホンアミダイト試薬、ヌクレオシドホスホ
ン酸モノエステル試薬（以下これら３つの試薬を総称し
てヌクレオチドユニットという）を用いて、必要ならば
第７工程に述べるチオエート化、メチルホスホネート化
及びメトキシエチルアミノ化する操作を実施して、前記
有効な配列の５’末端の一ヌクレオチド前までを結合さ
せた化合物（３）を得る方法である。[Group F] Adenine, guanine, cytosine, thymine and 5-methylcytosine B-1 method is the DNA of the 3'terminal portion of the effective nucleotide sequence.
Controlled pore glass (hereinafter referred to as CPG) having a linker used in a DNA synthesizer to which a nucleoside having a protecting group for synthesis (hereinafter referred to as 3′-terminal nucleoside) is attached, and commercially available for the DNA synthesizer. Nucleoside phosphoramidite reagent, nucleoside methylphosphonamidite reagent, nucleoside phosphonic acid monoester reagent (hereinafter, these three reagents are generically referred to as nucleotide units) are used, if necessary, thioate, methylphosphonate And methoxyethylamination are carried out to obtain a compound (3) in which the effective sequence is bound to the 5′-terminal up to one nucleotide.
【００５９】Ｂ−２法は炭素数２〜１０個の両末端に水
酸基を有するアルキレンジオール、あるいは保護した水
酸基やアミノ基の結合したアルキレンジオールの一方の
水酸基をジメトシキトリチル（ＤＭＴ）基で保護し、他
の水酸基にコハク酸無水物を作用させてコハク酸エステ
ルとする。このエステルのカルボキシル基にＣＰＧを結
合させ、末端のＤＭＴ基を除去したＣＰＧ担体（４−
６）にＤＮＡ合成機上でヌクレオチドユニットを順次反
応させて、必要ならば第７工程に述べるチオエート化、
メチルホスホネート化及びメトキシエチルアミノ化する
操作を実施して、前記有効な配列の５’末端の一ヌクレ
オチド前までを結合させた化合物（４ａ）を得る方法、
及びＣＰＧ担体（４−６）に３’末端ヌクレオチドユニ
ットを結合させる際にＤＮＡ合成機でチオエートヌクレ
オチドを得る時に用いられる一般的な反応操作を実施し
て３’末端ヌクレオシドをホスホロチオエート結合で結
合させた後、同様にヌクレオチドユニットを反応させて
（４ｂ）を得る方法である。In the method B-2, an alkylene diol having 2 to 10 carbon atoms and having hydroxyl groups at both ends, or one hydroxyl group of the protected hydroxyl group or the alkylene diol to which an amino group is bonded is protected with a dimethoxytrityl (DMT) group. Then, succinic anhydride is allowed to act on other hydroxyl groups to form a succinic acid ester. CPG carrier in which CPG is bound to the carboxyl group of this ester and the terminal DMT group is removed (4-
6) by sequentially reacting nucleotide units on a DNA synthesizer, and if necessary, thioation described in the 7th step,
A method of obtaining a compound (4a) in which up to one nucleotide before the 5'end of the effective sequence is bound by carrying out an operation of methylphosphonation and methoxyethylamination.
And a CPG carrier (4-6) having a 3'-terminal nucleotide unit attached thereto, a general reaction procedure used for obtaining a thioate nucleotide on a DNA synthesizer is performed to bond the 3'-terminal nucleoside with a phosphorothioate bond. And then similarly reacting nucleotide units to obtain (4b).
【００６０】Ｂ−３法はＢ−２法においてエチレングリ
コールとＣＰＧをコハク酸を介して結合させたＣＰＧ担
体（５−１）に３’末端ヌクレオシドの３’水酸基にホ
スホン酸をエステル結合させた化合物を結合させた後、
アルキルアミンと反応させて３’末端ヌクレオシドと
（５−１）をホスホロアミデート結合を介して結合させ
ＣＰＧ担体に順次ヌクレオチドユニットをＤＮＡ合成機
上で反応させ、必要ならば第７工程に述べるチオエート
化、メチルホスホネート化及びメトキシエチルアミノ化
する操作を実施して、前記有効な配列の５’末端の一ヌ
クレオチド前までを結合させた化合物（５）を得る方法
である。In the method B-3, the phosphonic acid was ester-bonded to the 3'hydroxyl group of the 3'terminal nucleoside on the CPG carrier (5-1) in which ethylene glycol and CPG were bonded via succinic acid in the method B-2. After binding the compound,
It is reacted with an alkylamine to bind the 3'-terminal nucleoside and (5-1) via a phosphoramidate bond, and the CPG carrier is sequentially reacted with nucleotide units on a DNA synthesizer, and if necessary, described in the seventh step. This is a method of obtaining a compound (5) in which thioate, methylphosphonate, and methoxyethylamination are carried out to bind the effective sequence up to one nucleotide before the 5'end.
【００６１】Ｂ−４法はヘキサエチレングリコールの一
方の水酸基をＤＭＴ化して、他方の水酸基にアミダイト
化試薬を反応させて、文献既知の（６−３）を得る。
（Ｎｕｃｌｅｉｃ Ａｃｉｄｓ Ｒｅｓ．１８ ６３５
３（１９９０）Ｍ．Ｄｕｒａｎｄほか） 次に前記ＤＭＴ化したヘキサエチレングリコール（６−
２）にＢ−３の方法と同じようにしてコハク酸を介して
ＣＰＧと結合させて、ＣＰＧ担体（６−６）を得る。In the method B-4, one hydroxyl group of hexaethylene glycol is converted to DMT, and the other hydroxyl group is reacted with an amidite-forming reagent to obtain (6-3) known in the literature.
(Nucleic Acids Res. 18 635
3 (1990) M.I. Durand et al.) Next, the hexaethylene glycol (6-
The CPG carrier (6-6) is obtained by binding to CPG via succinic acid in 2) in the same manner as in the method of B-3.
【００６２】（６−６）をＤＮＡ合成機上でＤＭＴ基を
除去した後、ヌクレオチドユニットと反応させ、必要な
らば第７工程に述べるチオエート化、メチルホスホネー
ト化及びメトキシエチルアミノ化する操作を実施して、
前記有効な配列の５’末端から一ヌクレオチド前までを
結合させた（６ａ）を得る。またＤＮＡ合成機上で（６
−６）のＤＭＴ基を除去した後、前記アミダイト体（６
−３）を１回，２回，３回反応させた後に同様にしてヌ
クレオチドユニットを反応させて、前記有効な配列の
５’末端から一ヌクレオチド前までを結合させて（６
ｂ），（６ｃ）、及び（６ｄ）を得る方法である。After removing the DMT group of (6-6) on a DNA synthesizer, it is reacted with a nucleotide unit, and if necessary, the operations of thioation, methylphosphonation and methoxyethylamination described in the seventh step are carried out. do it,
(6a) is obtained in which the 5'end of the effective sequence is linked to one nucleotide before. On the DNA synthesizer (6
After removing the DMT group of (6), the amidite (6
-3) is reacted once, twice or three times, and then similarly reacted with nucleotide units to bond from the 5′-terminal to the one nucleotide before the effective sequence (6
b), (6c), and (6d).
【００６３】Ｂ−５法は市販されている保護された２’
−デオキシヌクレオシドをリンカーを介して結合させた
ＣＰＧ（以下Ｄ''' −ＣＰＧという）のＤＭＴ基を除去
した後、Ｔｈｏｍａｓ Ｈｏｒｎらによって報告されて
いる（Ｔｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ，２
７，４７０５（１９８６））（２−シアノエトキシ）−
２−（２’−Ｏ−４，４’−ジメトキシトリチルオキシ
エチルスルホニル）エトキシ−Ｎ，Ｎ−ジイソプロピル
アミノホスフィン（７−１）を反応させて（７−３）を
得る。（７−３）のＤＭＴ基を除去した後、あらかじめ
合成された３’末端ヌクレオシドの３’水酸基にアリー
ル基あるいはアルキル基の結合したリン酸を結合させた
（７−４）を縮合剤を用いて結合させて（７−５）を得
た。（７−５）にヌクレオチドユニットを順次反応させ
て前記有効配列の５’末端の一ヌクレオチド前までを結
合させて（７ａ）を得る。Method B-5 is a commercially available protected 2 '
-After removing the DMT group of CPG (hereinafter referred to as D '''-CPG) to which deoxynucleoside is bound via a linker, reported by Thomas Horn et al. (Tetrahedron Letters, 2).
7 , 4705 (1986)) (2-cyanoethoxy)-
2- (2'-O-4,4'-dimethoxytrityloxyethylsulfonyl) ethoxy-N, N-diisopropylaminophosphine (7-1) is reacted to obtain (7-3). After removing the DMT group of (7-3), phosphoric acid having an aryl group or an alkyl group bonded to the 3'hydroxyl group of the 3'terminal nucleoside synthesized in advance was bonded to the compound (7-4) using a condensing agent. Combined to give (7-5). Nucleotide units are sequentially reacted with (7-5) to bind up to one nucleotide before the 5'end of the effective sequence to obtain (7a).
【００６４】また同様にして（７−３）のＤＭＴ基を除
去した後、あらかじめ合成しておいた３’−末端ヌクレ
オシドの３’位にアルキル、アリール、ホスホロアミダ
イトを有する（７−６）を反応させた後、ＤＮＡ合成機
上でリン酸トリエステルあるいはホスホロチオエートの
トリエステルを合成する場合と同じ処理を行い（７−
７）を得た。これにヌクレオチドユニットを順次反応さ
せて、必要ならば第７工程に述べるチオエート化、メチ
ルホスホネート化及びメトキシエチルアミノ化する操作
を実施して、前記有効配列の５’末端の一ヌクレオチド
前までを合成して（７ｂ）を得る方法である。Similarly, after the DMT group of (7-3) is removed, the 3'-terminal nucleoside synthesized in advance has an alkyl, aryl or phosphoramidite at the 3'position (7-6). And then the same treatment as in the case of synthesizing a phosphate triester or a phosphorothioate triester on a DNA synthesizer (7-
7) was obtained. Nucleotide units are sequentially reacted with this, and if necessary, the operations of thioation, methylphosphonation and methoxyethylamination described in step 7 are performed to synthesize up to one nucleotide before the 5'end of the effective sequence. Is a method of obtaining (7b).
【００６５】Ｃ−１法は化合物（２）に３価のリン酸化
剤を反応させて調製した３’亜リン酸誘導体（８）とＢ
−１〜Ｂ−５法で合成したＣＰＧに担持されたオリゴマ
ーである（３），（４ａ〜ｂ），（５），（６ａ〜
ｄ），（７ａ）及び（７ｂ）を酸化剤を用いて酸化した
後、必要ならば第７工程に述べるチオエート化、メチル
ホスホネート化及びメトキシエチルアミノ化する操作を
実施して、ＣＰＧから切出した後、５’末端の５’炭素
に結合した置換分以外の保護基を除去して一般式（１）
で表わされる化合物を製造する方法である。Method C-1 is a 3'phosphorous acid derivative (8) prepared by reacting compound (2) with a trivalent phosphorylating agent and B.
(3), (4a-b), (5), (6a-, which are oligomers supported on CPG synthesized by the methods -1 to B-5.
After d), (7a) and (7b) were oxidized with an oxidizing agent, the procedures of thioation, methylphosphonation and methoxyethylamination described in the seventh step were carried out to cut out from CPG, if necessary. Thereafter, the protecting group other than the substituent bonded to the 5'carbon at the 5'end is removed to give the compound represented by the general formula (1)
Is a method for producing a compound represented by.
【００６６】Ｃ−２法は化合物（２）にリン酸化剤を反
応させて調製した３’−リン酸誘導体（９）と前記化合
物（３），（４ａ〜ｂ），（５），（６ａ〜ｄ），（７
ａ）及び（７ｂ）のＤＭＴ基のみを除去したものを縮合
剤を用いて縮合させ、リン酸トリエステル結合を形成さ
せて、ＣＰＧから切り出す操作を行ない、５’末端の
５’炭素に結合した置換分以外の保護基を除去して、通
常の精製法により精製して目的の化合物（１）を得る方
法である。In the method C-2, the 3'-phosphate derivative (9) prepared by reacting the compound (2) with a phosphorylating agent and the compounds (3), (4a-b), (5) and (6a). ~ D), (7
Those obtained by removing only the DMT groups of a) and (7b) are condensed with a condensing agent to form a phosphate triester bond, and the CPG is cleaved to bond to the 5'carbon at the 5'end. In this method, the protective group other than the substituent is removed, and the desired compound (1) is obtained by purification by a conventional purification method.
【００６７】Ｃ−３法は化合物（２）の３’位にホスホ
ン酸基を導入した化合物（１０）と前記化合物（３），
（４ａ〜ｂ），（５），（６ａ〜ｄ），（７ａ）及び
（７ｂ）のＤＭＴ基のみを除去したものを塩基の存在下
に酸ハライドと反応させて縮合し、酸化剤によりリン酸
ジエステル結合を形成させるか又は必要ならば第７工程
に述べるチオエート化及びメトキシエチルアミノ化する
操作を実施して、ＣＰＧから切り出す操作を行ない、
５’末端の５’炭素に結合した置換分以外の保護基を除
去して、通常の精製法により精製して、目的化合物
（１）を得る方法である。Method C-3 is the compound (10) having a phosphonic acid group introduced at the 3'position of the compound (2) and the compound (3),
(4a-b), (5), (6a-d), (7a) and (7b), in which only the DMT group is removed, are reacted with an acid halide in the presence of a base to condense, and phosphorus is added by an oxidizing agent. The acid diester bond is formed or, if necessary, the operation of thioation and methoxyethylamination described in the seventh step is carried out to carry out the operation of cleaving from CPG,
In this method, the protecting group other than the substituent bonded to the 5'carbon at the 5'end is removed, and the compound of interest (1) is obtained by purification by a conventional purification method.
【００６８】以下にＡ法からＣ法について詳しく説明す
る。The methods A to C will be described in detail below.
【００６９】Ａ乃至Ｃ法の工程表において、Ｒ1 ，Ｒ
2 ，Ｒ3 ，Ｒ4 ，Ｚ，Ｙ1 ，Ｙ2 ，Ｙ3 ，Ｙ4 ，Ｘ，
ｎ，ｍ及びＢは前述のものと同意義を示し、Ａ1 は一般
にヌクレオシドの一級の水酸基を特異的に保護するため
に用いられるトリチル基（Ｔｒ）、モノメトキシトリチ
ル（ＭＭＴ）基、ジメトキシトリチル（ＤＭＴ）基を示
す。Ａ2 は三級ブチルジメチルシリル（ＴＢＤＭＳ）基
やトリイソプロピルシリル（ＴＩＰＳ）基のような３置
換シリル基、トリクロロエトキシカルボニル（Ｔｒｏ
ｃ）基のようなトリハロゲノエトキシカルボニル基、ベ
ンジルオキシカルボニル（Ｚ）基のようなアラルキルオ
キシカルボニル基を示す。In the process charts of the methods A to C, R 1 , R
2 , R 3 , R 4 , Z, Y 1 , Y 2 , Y 3 , Y 4 , X,
n, m, and B have the same meanings as described above, and A 1 is a trityl group (Tr), a monomethoxytrityl (MMT) group, or dimethoxytrityl, which is generally used to specifically protect the primary hydroxyl group of a nucleoside. A (DMT) group is shown. A 2 is a tri-substituted silyl group such as a tertiary butyldimethylsilyl (TBDMS) group or a triisopropylsilyl (TIPS) group, trichloroethoxycarbonyl (Tro).
It represents a trihalogenoethoxycarbonyl group such as group c) and an aralkyloxycarbonyl group such as a benzyloxycarbonyl (Z) group.
【００７０】Ｄ’は前記有効な塩基配列のＤＮＡ合成の
ためにアミノ基がアシル基で保護された５’末端側ヌク
レオチドの塩基を示し、Ｄ''は同じく３’末端側ヌクレ
オチドの塩基部分を示し、Ｄ''' はＤＮＡ合成に用いら
れる任意のヌクレオチドユニットの塩基部分を示し、下
記のＦ群から選択される塩基、又は保護された相同の塩
基を示す。D'represents the base of the 5'terminal nucleotide in which the amino group is protected by an acyl group for DNA synthesis of the above-mentioned effective base sequence, and D "is the base portion of the 3'terminal nucleotide. D '''represents a base portion of an arbitrary nucleotide unit used for DNA synthesis, and represents a base selected from the following F group or a protected homologous base.
【００７１】Ｆは前記有効な塩基配列の５’末端側の一
ヌクレオチドを除いたオリゴヌクレオチド部分で、塩基
部分及び／又はリン酸部分が保護基によって保護された
相同のオリゴヌクレオチド、部分的にチオエート化ある
いはメチルホスホネート化あるいはメトキシエチルアミ
ノホスフェート化されたオリゴヌクレオチドを示すが、
５’−末端ヌクレオシドの５’位水酸基と３’末端ヌク
レオシドの３’位水酸基は含まぬものとする。Ｖはリン
酸部分の保護基を示し、Ｕは同じくアミダイト部分のア
ミノ基を示す。Ｗ1 〜Ｗ5 はＢ−１〜Ｂ−５に示した方
法において最終目的化合物のＣＰＧからオリゴヌクレオ
チドＦの３’末端部分の３’水酸基の酸素原子までを示
す。ｌは１〜９の整数を示し、Ｅは水素原子又は、保護
されていてもよい水酸基あるいはアミノ基を示し、Ｋは
酸素又は硫黄原子を示す。F is an oligonucleotide moiety except for one nucleotide on the 5'-terminal side of the effective base sequence, a homologous oligonucleotide in which the base moiety and / or the phosphate moiety is protected by a protecting group, and a partial thioate. Shows an oligonucleotide modified or methylphosphonate-modified or methoxyethylaminophosphate-modified,
The 5'-hydroxyl group of the 5'-terminal nucleoside and the 3'-hydroxyl group of the 3'-terminal nucleoside are not included. V represents a protecting group for the phosphoric acid moiety, and U also represents an amino group for the amidite moiety. W 1 to W 5 are from the CPG of the final target compound to the oxygen atom of the 3 ′ hydroxyl group at the 3 ′ end portion of the oligonucleotide F in the method shown in B- 1 to B-5. l represents an integer of 1 to 9, E represents a hydrogen atom or an optionally protected hydroxyl group or amino group, and K represents an oxygen or sulfur atom.
【００７２】Ｒ5 はメチル、エチル、プロピル、ブチ
ル、フェニル，メトキシ、エトキシ、プロポキシ、ブト
キシ、シアノエチルオキシあるいは置換されていてもよ
いフェニルオキシ基を示す。R 5 represents methyl, ethyl, propyl, butyl, phenyl, methoxy, ethoxy, propoxy, butoxy, cyanoethyloxy or an optionally substituted phenyloxy group.
【００７３】［Ｆ群］ アデニン、グアニン、シトシン、チミン及び５−メチル
シトシン 以下に各工程につき、さらに詳細に説明する。なお、同
様にして行うことができる工程については、最先のもの
を代表として説明する。[Group F] Adenine, guanine, cytosine, thymine and 5-methylcytosine Each step will be described in more detail below. In addition, about the process which can be performed similarly, the earliest thing is demonstrated as a representative.
【００７４】（第１、８、１８工程）本工程は、不活性
溶剤中、化合物（２−１）（但し、塩基部分がＡ、Ｇ、
Ｃの場合は、存在するアミノ基のアシル化保護工程を前
段階に含む。保護工程は、公知の方法（ J. Am. Chem.S
oc.,104,1316,(1982))により容易に実施することができ
る。アミノ基の保護基としては、一般に低級脂肪族アシ
ル又は芳香族アシルが用いられる。使用される低級脂肪
族アシルとしては、例えば、ホルミル、アセチル、プロ
ピオニル、ブチリル、イソブチリル、ペンタノイル、ピ
バロイル、バレリル、イソバレリル基などがあげられ、
使用される芳香族アシルとしては、例えば、ベンゾイ
ル、４−アセトキシベンゾイル、４−メトキシベンゾイ
ル、４−メチルベンゾイル、１−ナフトイルなどがあげ
られ、好適には、塩基部分がＡ、Ｃの場合はベンゾイル
基、Ｇの場合はイソブチリル基である。）に、水酸基の
保護化試薬を反応させて、選択的に５’位の水酸基のみ
を保護した化合物（２−２）を製造する工程である。(Steps 1, 8, and 18) In this step, compound (2-1) (provided that the base moiety is A, G,
In the case of C, the step of acylating and protecting the existing amino group is included in the preceding step. The protection step is a known method (J. Am. Chem.S.
oc., 104, 1316, (1982)). As the amino group-protecting group, lower aliphatic acyl or aromatic acyl is generally used. Examples of the lower aliphatic acyl used include formyl, acetyl, propionyl, butyryl, isobutyryl, pentanoyl, pivaloyl, valeryl and isovaleryl groups.
Examples of the aromatic acyl used include benzoyl, 4-acetoxybenzoyl, 4-methoxybenzoyl, 4-methylbenzoyl, 1-naphthoyl, etc., and preferably benzoyl when the base moiety is A or C. And G is an isobutyryl group. ) Is reacted with a hydroxyl group-protecting reagent to selectively produce a compound (2-2) in which only the 5'-position hydroxyl group is protected.
【００７５】使用される溶剤としては、好適には、ベン
ゼン、トルエン、キシレンのような芳香族炭化水素類；
メチレンクロリド、クロロホルム、四塩化炭素、ジクロ
ロエタン、クロロベンゼン、ジクロロベンゼンのような
ハロゲン化炭化水素類；蟻酸エチル、酢酸エチル、酢酸
プロピル、酢酸ブチル、炭酸ジエチルのようなエステル
類；ジエチルエ−テル、ジイソプロピルエ−テル、テト
ラヒドロフラン、ジオキサン、ジメトキシエタン、ジエ
チレングリコールジメチルエーテルのようなエ−テル
類；アセトン、メチルエチルケトン、メチルイソブチル
ケトン、イソホロン、シクロヘキサノンのようなケトン
類；ニトロエタン、ニトロベンゼンのようなニトロ化合
物類；アセトニトリル、イソブチロニトリルのようなニ
トリル類；ホルムアミド、ジメチルホルムアミド（ＤＭ
Ｆ）、ジメチルアセトアミド、ヘキサメチルホスホロト
リアミドのようなアミド類；ジメチルスルホキシド、ス
ルホランのようなスルホキシド類；トリメチルアミン、
トリエチルアミン、Ｎ−メチルモルホリン等の脂肪族三
級アミン類；ピリジン、ピコリンのような芳香族アミン
などがあげられ、さらに好適には、ハロゲン化炭化水素
類（特にメチレンクロリド）、アミド類（特にＤＭＦ）
である。The solvent used is preferably aromatic hydrocarbons such as benzene, toluene and xylene;
Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; diethyl ether, diisopropyl ether Ethers such as ter, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone; nitro compounds such as nitroethane, nitrobenzene; acetonitrile, iso Nitriles such as butyronitrile; formamide, dimethylformamide (DM
F), amides such as dimethylacetamide, hexamethylphosphorotriamide; sulfoxides such as dimethylsulfoxide, sulfolane; trimethylamine,
Aliphatic tertiary amines such as triethylamine and N-methylmorpholine; aromatic amines such as pyridine and picoline, and more preferably halogenated hydrocarbons (especially methylene chloride) and amides (especially DMF). )
Is.
【００７６】使用される保護化試薬としては、５’位の
みを選択的に保護でき、酸性、中性の条件下、除去でき
るものであれば、特に制限はないが、好適には、トリチ
ルクロリド、モノメトキシトリチルクロリド、ジメトキ
シトリチルクロリドのようなトリアリールメチルハライ
ド類である。The protecting reagent used is not particularly limited as long as it can selectively protect only the 5'position and can be removed under acidic or neutral conditions, but preferably trityl chloride is used. , Monomethoxytrityl chloride and dimethoxytrityl chloride.
【００７７】保護化試薬として、トリアリールメチルハ
ライド類を用いる場合には、通常、塩基を用いる。When a triarylmethyl halide is used as the protecting reagent, a base is usually used.
【００７８】使用される塩基としては、ピリジン、ジメ
チルアミノピリジン、ピロリジノピリジン等の複素環ア
ミン類、トリメチルアミン、トリエチルアミン等の脂肪
族三級アミン類があげられ、好適には、有機塩基類（特
にピリジン、ジメチルアミノピリジン、ピロリジノピリ
ジン）である。Examples of the base used include heterocyclic amines such as pyridine, dimethylaminopyridine and pyrrolidinopyridine, and aliphatic tertiary amines such as trimethylamine and triethylamine. Preferably, organic bases (especially Pyridine, dimethylaminopyridine, pyrrolidinopyridine).
【００７９】溶剤として有機アミン類を用いる場合に
は、有機アミン類自体が脱酸剤として働くので、改めて
他の脱酸剤を加える必要はない。When organic amines are used as the solvent, the organic amines themselves act as a deoxidizing agent, so that it is not necessary to add another deoxidizing agent.
【００８０】反応温度は使用される原料、試薬、溶剤な
どにより通常０乃至１５０℃であり、好適には２０乃至
１００℃である。The reaction temperature is usually 0 to 150 ° C., preferably 20 to 100 ° C., depending on the starting materials, reagents and solvents used.
【００８１】反応時間は使用される原料、溶剤、反応温
度などにより異なるが、通常１乃至１００時間であり、
好適には、２乃至２４時間である。The reaction time varies depending on the raw materials used, the solvent, the reaction temperature, etc., but is usually 1 to 100 hours,
It is preferably 2 to 24 hours.
【００８２】反応終了後、たとえば、反応液を水に注
ぎ、水と混和しない溶剤、たとえばベンゼン、エ−テ
ル、酢酸エチルなどで抽出し、抽出液より溶剤を留去す
ることによって得られるものを、通常、そのまま次の工
程に用いる。所望により、各種クロマトあるいは再結晶
法により、単離精製することもできる。After completion of the reaction, for example, the product obtained by pouring the reaction solution into water, extracting with a solvent immiscible with water, for example, benzene, ether, ethyl acetate, etc., and distilling the solvent off from the extract solution is used. Ordinarily, it is directly used in the next step. If desired, it can be isolated and purified by various chromatographic methods or recrystallization methods.
【００８３】（第２工程）本工程は、不活性溶剤中、化
合物（２−２）に水酸基の保護化試薬を反応させて、化
合物（２−３）を製造する工程である。(Second Step) This step is a step of reacting compound (2-2) with a hydroxyl group protecting reagent in an inert solvent to produce compound (2-3).
【００８４】使用される溶剤としては、好適には、ベン
ゼン、トルエン、キシレンのような芳香族炭化水素類；
メチレンクロリド、クロロホルム、四塩化炭素、ジクロ
ロエタン、クロロベンゼン、ジクロロベンゼンのような
ハロゲン化炭化水素類；蟻酸エチル、酢酸エチル、酢酸
プロピル、酢酸ブチル、炭酸ジエチルのようなエステル
類；ジエチルエ−テル、ジイソプロピルエ−テル、テト
ラヒドロフラン、ジオキサン、ジメトキシエタン、ジエ
チレングリコールジメチルエーテルのようなエ−テル
類；アセトン、メチルエチルケトン、メチルイソブチル
ケトン、イソホロン、シクロヘキサノンのようなケトン
類；ニトロエタン、ニトロベンゼンのようなニトロ化合
物類；アセトニトリル、イソブチロニトリルのようなニ
トリル類；ホルムアミド、ジメチルホルムアミド、ジメ
チルアセトアミド、ヘキサメチルホスホロトリアミドの
ようなアミド類；ジメチルスルホキシド、スルホランの
ようなスルホキシド類があげられ、さらに好適には、エ
ーテル類（特にテトラヒドロフラン）、ハロゲン化炭化
水素類（特に塩化メチレン）、芳香族炭化水素類（特に
トルエン）、アミド類（特にDMF ）があげられる。The solvent used is preferably aromatic hydrocarbons such as benzene, toluene and xylene;
Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; diethyl ether, diisopropyl ether Ethers such as ter, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone; nitro compounds such as nitroethane, nitrobenzene; acetonitrile, iso Nitriles such as butyronitrile; amides such as formamide, dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide; Examples thereof include sulfoxides such as tyl sulfoxide and sulfolane, and more preferably ethers (particularly tetrahydrofuran), halogenated hydrocarbons (particularly methylene chloride), aromatic hydrocarbons (particularly toluene), amides (particularly DMF).
【００８５】使用される保護化試薬としては、通常、
５’位の保護基と区別して脱保護できるものであれば、
特に制限はないが、好適には、ｔ−ブチルジメチルシリ
ルクロリドあるいはトリイソプロピルシリルクロリドの
ようなシリルハライド類、トリクロロエトキシカルボニ
ルクロリドのようなハロアルコキシカルボニルハライド
類や、ベンジルオキシカルボニルクロリドのようなアラ
ルキルオキシカルボニルハライド類があげられる。The protecting reagent used is usually
If it can be deprotected in distinction from the protecting group at the 5'position,
Although not particularly limited, preferably, silyl halides such as t-butyldimethylsilyl chloride or triisopropylsilyl chloride, haloalkoxycarbonyl halides such as trichloroethoxycarbonyl chloride, and aralkyl such as benzyloxycarbonyl chloride. Examples thereof include oxycarbonyl halides.
【００８６】保護化試薬として、シリルハライド類、ハ
ロアルコキシカルボニルハライド類やアラルキルオキシ
カルボニルハライド類を用いる場合には、通常、塩基を
用いる。When silyl halides, haloalkoxycarbonyl halides or aralkyloxycarbonyl halides are used as the protecting reagent, a base is usually used.
【００８７】使用される塩基としては、好適には、有機
塩基類（特にトリエチルアミン、ピリジン、Ｎ−メチル
モルホリン、ＤＢＵ及びイミダゾールなど）である。The base used is preferably an organic base (especially triethylamine, pyridine, N-methylmorpholine, DBU and imidazole).
【００８８】反応温度は使用される試薬、原料、溶剤な
どにより通常−２０乃至１５０℃であり、好適には−１
０乃至５０℃である。The reaction temperature is usually -20 to 150 ° C, preferably -1 depending on the reagents, raw materials, solvent and the like used.
It is 0 to 50 ° C.
【００８９】反応時間は使用される原料、溶剤、反応温
度などにより異なるが、通常１乃至１００時間であり、
好適には、１乃至２４時間である。The reaction time varies depending on the starting materials used, the solvent, the reaction temperature, etc., but is usually 1 to 100 hours,
It is preferably 1 to 24 hours.
【００９０】反応終了後、たとえば、反応液を水に注
ぎ、水と混和しない溶剤、たとえばベンゼン、エ−テ
ル、酢酸エチルなどで抽出し、抽出液より溶剤を留去す
ることによって得られるものを、通常、そのまま次の工
程に用いる。所望により、各種クロマトあるいは再結晶
法により、単離精製することもできる。After completion of the reaction, for example, the reaction solution may be obtained by pouring the reaction solution into water, extracting with a solvent immiscible with water, such as benzene, ether, ethyl acetate, etc., and distilling the solvent off from the extraction solution. Ordinarily, it is directly used in the next step. If desired, it can be isolated and purified by various chromatographic methods or recrystallization methods.
【００９１】（第３、１１、２２、２５工程）本工程
は、不活性溶剤中、化合物（２−３）、（４−５）、
（６−６）又は（６−８）に脱保護化試薬を反応させ
て、５’位の水酸基の保護基を選択的に除去して、対応
の化合物（２−４）、（４−６）、（６−７）又は（６
−９）を製造する工程である。(3rd, 11th, 22nd and 25th Steps) In this step, the compounds (2-3), (4-5), and
(6-6) or (6-8) is reacted with a deprotecting reagent to selectively remove the protecting group for the hydroxyl group at the 5'-position to give the corresponding compound (2-4), (4-6) ), (6-7) or (6
-9) is a process of manufacturing.
【００９２】使用される溶剤としては、好適には、ベン
ゼン、トルエン、キシレンのような芳香族炭化水素類；
メチレンクロリド、クロロホルム、四塩化炭素、ジクロ
ロエタン、クロロベンゼン、ジクロロベンゼンのような
ハロゲン化炭化水素類；蟻酸エチル、酢酸エチル、酢酸
プロピル、酢酸ブチル、炭酸ジエチルのようなエステル
類；ジエチルエ−テル、ジイソプロピルエ−テル、テト
ラヒドロフラン、ジオキサン、ジメトキシエタン、ジエ
チレングリコールジメチルエーテルのようなエ−テル
類；メタノ−ル、エタノ−ル、n-プロパノ−ル、イソプ
ロパノ−ル、n-ブタノ−ル、イソブタノ−ル、t-ブタノ
−ル、イソアミルアルコ−ル、ジエチレングリコール、
グリセリン、オクタノール、シクロヘキサノール、メチ
ルセロソルブ、のようなアルコ−ル類；アセトン、メチ
ルエチルケトン、メチルイソブチルケトン、イソホロ
ン、シクロヘキサノンのようなケトン類；ニトロエタ
ン、ニトロベンゼンのようなニトロ化合物類；アセトニ
トリル、イソブチロニトリルのようなニトリル類；ホル
ムアミド、ジメチルホルムアミド、ジメチルアセトアミ
ド、ヘキサメチルホスホロトリアミドのようなアミド
類；ジメチルスルホキシド、スルホランのようなスルホ
キシド類があげられ、さらに好適には、アルコ−ル類
（特にメタノール、エタノール）や塩化メチレン及び脱
保護化試薬として酢酸を用いる場合は酢酸と水の混液が
あげられる。The solvent used is preferably an aromatic hydrocarbon such as benzene, toluene or xylene;
Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; diethyl ether, diisopropyl ether -Ethers, tetrahydrofuran, dioxane, dimethoxyethane, ethers such as diethylene glycol dimethyl ether; methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t- Butanol, isoamyl alcohol, diethylene glycol,
Alcohols such as glycerin, octanol, cyclohexanol, methyl cellosolve; Ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone; Nitro compounds such as nitroethane, nitrobenzene; Acetonitrile, isobutyro Nitriles such as nitriles; amides such as formamide, dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide; sulfoxides such as dimethyl sulfoxide and sulfolane, and more preferably alcohols (particularly When acetic acid is used as a deprotecting reagent, it may be a mixture of acetic acid and water.
【００９３】使用される脱保護化試薬としては、通常用
いられるものであれば、特に制限はないが、保護基がト
リアリールメチル基の場合には、例えば酢酸、ジクロロ
酢酸、トリフルオロ酢酸、塩酸、及び臭化亜鉛のような
ルイス酸があげられ、好適には酢酸、ジクロロ酢酸、ト
リフルオロ酢酸である。The deprotecting reagent used is not particularly limited as long as it is a commonly used one, but when the protecting group is a triarylmethyl group, for example, acetic acid, dichloroacetic acid, trifluoroacetic acid, hydrochloric acid. , And Lewis acids such as zinc bromide, and acetic acid, dichloroacetic acid and trifluoroacetic acid are preferred.
【００９４】反応温度は使用される試薬、原料、溶剤な
どにより異なるが、通常−１０乃至１００℃であり、好
適には０乃至５０℃である。The reaction temperature will differ depending on the reagents, starting materials, solvent, etc. used, but is usually -10 to 100 ° C., and preferably 0 to 50 ° C.
【００９５】反応時間は使用される原料、溶剤、反応温
度などにより異なるが、通常１分間乃至５０時間であ
り、好適には、１分間乃至２４時間である。The reaction time will differ depending on the starting materials used, solvent, reaction temperature, etc., but is usually 1 minute to 50 hours, and preferably 1 minute to 24 hours.
【００９６】反応終了後、たとえば、反応液をピリジン
等の塩基を用いて中和し、水に注ぎ、水と混和しない溶
剤、たとえばベンゼン、エ−テル、酢酸エチルなどで抽
出し、抽出液より溶剤を留去することによって得られる
ものを、通常、そのまま次の工程に用いる。所望によ
り、各種クロマトあるいは再結晶法により、単離精製す
ることもできる。After completion of the reaction, for example, the reaction solution is neutralized with a base such as pyridine, poured into water, extracted with a solvent immiscible with water such as benzene, ether, ethyl acetate, etc. The substance obtained by distilling off the solvent is usually used as it is in the next step. If desired, it can be isolated and purified by various chromatographic methods or recrystallization methods.
【００９７】第１１、２２及び２５工程においては、目
的物は濾取により集められ、メチレンクロリドのような
有機溶剤で洗浄され、そのまま、次の工程に用いられ
る。In steps 11, 22 and 25, the desired product is collected by filtration, washed with an organic solvent such as methylene chloride and used as it is in the next step.
【００９８】（第４、６工程）本工程は、不活性溶剤
中、塩基の存在下、化合物（２−１）又は（２−４）に
化合物（２−５）（式中、Hal はハロゲン原子を示
す。）を反応させて、化合物（２）又は（２−６）を製
造する工程である。(Steps 4 and 6) In this step, the compound (2-1) or (2-4) is added to the compound (2-5) in the presence of a base in an inert solvent (wherein Hal is halogen). Atoms are shown) to produce compound (2) or (2-6).
【００９９】使用される化合物（２−５）のハライド部
分としては、塩素、臭素、ヨウ素があげられ、好適には
塩素および臭素である。The halide moiety of the compound (2-5) used includes chlorine, bromine and iodine, preferably chlorine and bromine.
【０１００】使用される溶剤としては、好適には、ベン
ゼン、トルエン、キシレンのような芳香族炭化水素類；
メチレンクロリド、クロロホルム、四塩化炭素、ジクロ
ロエタン、クロロベンゼン、ジクロロベンゼンのような
ハロゲン化炭化水素類；蟻酸エチル、酢酸エチル、酢酸
プロピル、酢酸ブチル、炭酸ジエチルのようなエステル
類；ジエチルエ−テル、ジイソプロピルエ−テル、テト
ラヒドロフラン、ジオキサン、ジメトキシエタン、ジエ
チレングリコールジメチルエーテルのようなエ−テル
類；アセトン、メチルエチルケトン、メチルイソブチル
ケトン、イソホロン、シクロヘキサノンのようなケトン
類；ニトロエタン、ニトロベンゼンのようなニトロ化合
物類；アセトニトリル、イソブチロニトリルのようなニ
トリル類；ホルムアミド、ジメチルホルムアミド、ジメ
チルアセトアミド、ヘキサメチルホスホロトリアミドの
ようなアミド類；ジメチルスルホキシド、スルホランの
ようなスルホキシド類があげられ、さらに好適には、エ
−テル類（特にテトラヒドロフラン）、ケトン類（特
に、アセトン）、ハロゲン化炭化水素類（特にメチレン
クロリド）、アミド類（特にＤＭＦ）及び芳香族アミン
類（特にピリジン）である。The solvent used is preferably an aromatic hydrocarbon such as benzene, toluene or xylene;
Halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, dichloroethane, chlorobenzene, dichlorobenzene; esters such as ethyl formate, ethyl acetate, propyl acetate, butyl acetate, diethyl carbonate; diethyl ether, diisopropyl ether Ethers such as ter, tetrahydrofuran, dioxane, dimethoxyethane, diethylene glycol dimethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, isophorone, cyclohexanone; nitro compounds such as nitroethane, nitrobenzene; acetonitrile, iso Nitriles such as butyronitrile; amides such as formamide, dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide; Examples thereof include sulfoxides such as tyl sulfoxide and sulfolane, and more preferably, ethers (particularly tetrahydrofuran), ketones (particularly acetone), halogenated hydrocarbons (particularly methylene chloride), amides (particularly DMF) and aromatic amines (especially pyridine).
【０１０１】使用される塩基としては、好適には、有機
塩基類（特にトリエチルアミン、ピリジン、Ｎ−メチル
モルホリン、ＤＢＵなど）、アルカリ金属水素化物（特
に、水素化ナトリウム）及びアルカリ金属炭酸塩（特
に、炭酸ナトリウム、炭酸リチウム）であるが、化合物
（２−５）のＺが珪素原子の場合は、イミダゾールのよ
うな有機塩基が最も好ましい。The base used is preferably organic bases (especially triethylamine, pyridine, N-methylmorpholine, DBU etc.), alkali metal hydrides (especially sodium hydride) and alkali metal carbonates (especially , Sodium carbonate, lithium carbonate), but when Z in the compound (2-5) is a silicon atom, an organic base such as imidazole is most preferable.
【０１０２】反応温度は、特に限定はないが、通常０℃
から100 ℃であり、好適に、２０乃至６０℃で実施す
る。The reaction temperature is not particularly limited, but is usually 0 ° C.
To 100 ° C, preferably 20 to 60 ° C.
【０１０３】反応時間は、通常５分から３０時間である
が、反応を５０℃で実施したときには、１０時間で反応
は終了する。The reaction time is usually 5 minutes to 30 hours, but when the reaction is carried out at 50 ° C., the reaction is completed in 10 hours.
【０１０４】例えば、反応終了後、反応混合物を適宜中
和し、又、不溶物が存在する場合には濾過により除去し
た後、水と酢酸エチルのような混和しない有機溶媒を加
え、水洗後、、目的化合物を含む有機層を分離し、無水
硫酸マグネシウム等で乾燥後、溶剤を留去することによ
って得られる。得られた目的化合物は必要ならば、常
法、例えば再結晶、再沈殿又はクロマトグラフィ−等に
よって更に精製できる。For example, after completion of the reaction, the reaction mixture is appropriately neutralized, and if insoluble matter is present, it is removed by filtration, water and an immiscible organic solvent such as ethyl acetate are added, and after washing with water, The organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate or the like, and then the solvent is distilled off. If necessary, the obtained target compound can be further purified by a conventional method, for example, recrystallization, reprecipitation or chromatography.
【０１０５】（第５工程）本工程は、不活性溶剤中、化
合物（２−６）に脱保護剤を反応させて、化合物（２）
を製造する工程である。(Fifth Step) In this step, compound (2-6) is reacted with a deprotecting agent in an inert solvent to give compound (2).
Is a process of manufacturing.
【０１０６】１）３’位の保護基として、シリル類を使
用した場合には、通常、弗化テトラブチルアンモニウム
のような弗化物イオンを生成する化合物で処理すること
により除去される。使用される溶剤としては、反応を阻
害しないものであれば特に限定はないが、テトラヒドロ
フラン、ジオキサンのようなエ−テル類が好適である。1) When a silyl compound is used as a protecting group at the 3'-position, it is usually removed by treating with a compound which produces a fluoride ion such as tetrabutylammonium fluoride. The solvent used is not particularly limited as long as it does not inhibit the reaction, but ethers such as tetrahydrofuran and dioxane are preferable.
【０１０７】反応温度は、特に限定はないが、通常−３
０℃から100 ℃であり、好適に、０℃乃至３０℃で実施
する。Although the reaction temperature is not particularly limited, it is usually -3.
The temperature is from 0 ° C to 100 ° C, preferably 0 ° C to 30 ° C.
【０１０８】反応時間は、通常５分から３０時間である
が、反応を２０℃で実施したときには、１０時間で反応
は終了する。The reaction time is usually 5 minutes to 30 hours, but when the reaction is carried out at 20 ° C., the reaction is completed in 10 hours.
【０１０９】例えば、反応終了後、反応混合物を適宜中
和し、又、不溶物が存在する場合には濾過により除去し
た後、水と酢酸エチルのような混和しない有機溶媒を加
え、水洗後、、目的化合物を含む有機層を分離し、無水
硫酸マグネシウム等で乾燥後、溶剤を留去することによ
って得られる。得られた目的化合物は必要ならば、常
法、例えば再結晶、再沈殿又はクロマトグラフィ−等に
よって更に精製できる。For example, after completion of the reaction, the reaction mixture is appropriately neutralized, and if insoluble matter is present, it is removed by filtration, water and an immiscible organic solvent such as ethyl acetate are added, and after washing with water, The organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate or the like, and then the solvent is distilled off. If necessary, the obtained target compound can be further purified by a conventional method, for example, recrystallization, reprecipitation or chromatography.
【０１１０】２）３’位の保護基としてハロアルコキシ
カルボニル基を使用した場合には、通常、亜鉛末を用い
る。2) When a haloalkoxycarbonyl group is used as the 3'-protecting group, zinc powder is usually used.
【０１１１】使用される溶剤としては、反応を阻害しな
いものであれば特に限定はないが、酢酸、アルコール又
はこれらと水との混合溶剤が好適である。The solvent used is not particularly limited as long as it does not inhibit the reaction, but acetic acid, alcohol or a mixed solvent of these and water is preferable.
【０１１２】反応温度は、特に限定はないが、通常０℃
から100 ℃であり、好適には、室温で実施する。The reaction temperature is not particularly limited, but is usually 0 ° C.
To 100 ° C., preferably at room temperature.
【０１１３】反応時間は、通常５分から３０時間である
が、反応を室温で実施したときには、１０時間で反応は
終了する。The reaction time is usually 5 minutes to 30 hours, but when the reaction is carried out at room temperature, the reaction is completed in 10 hours.
【０１１４】例えば、反応終了後、反応混合物を適宜中
和し、又、不溶物が存在する場合には濾過により除去し
た後、水と酢酸エチルのような混和しない有機溶媒を加
え、水洗後、目的化合物を含む有機層を分離し、無水硫
酸マグネシウム等で乾燥後、溶剤を留去することによっ
て得られる。得られた目的化合物は必要ならば、常法、
例えば再結晶、再沈殿又はクロマトグラフィ−等によっ
て更に精製できる。For example, after the completion of the reaction, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, water and an immiscible organic solvent such as ethyl acetate are added, and after washing with water, The organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate or the like, and then the solvent is distilled off. If necessary, the obtained target compound is subjected to a conventional method,
It can be further purified by, for example, recrystallization, reprecipitation or chromatography.
【０１１５】３）３’位の脱保護としてアラルキルオキ
シカルボニル基類を使用した場合には、接触還元又は酸
化によって行なうことができる。3) When an aralkyloxycarbonyl group is used for deprotection at the 3'position, it can be carried out by catalytic reduction or oxidation.
【０１１６】接触還元を行なう場合に使用される還元触
媒としては、通常、接触還元反応に使用されるものであ
れば、特に限定はないが、好適には、パラジウム炭素、
ラネ−ニッケル、酸化白金、白金黒、ロジウム−酸化ア
ルミニウム、トリフェニルホスフィン−塩化ロジウム、
パラジウム−硫酸バリウムが用いられる。圧力は、特に
限定はないが、通常１乃至１０気圧で行なわれる。反応
温度及び反応時間は、出発物質、溶媒及び触媒の種類等
により異なるが、通常、０乃至１００℃で、５分乃至２
４時間実施される。酸化による除去において使用される
溶剤としては、本反応に関与しないものであれば特に限
定はないが、好適には、含水有機溶剤である。このよう
な有機溶剤として好適には、アセトンのようなケトン
類、メチレンクロリド、クロロホルム、四塩化炭素のよ
うなハロゲン化炭化水素類、アセトニトリルのようなニ
トリル類、ジエチルエ−テル、テトラヒドロフラン、ジ
オキサンのようなエ−テル類、ジメチルホルムアミド、
ジメチルアセトアミド、ヘキサメチルホスホロトリアミ
ドのようなアミド類及びジメチルスルホキシドのような
スルホキシド類を挙げることができる。使用される酸化
剤としては、酸化に使用される化合物であれば特に限定
はないが、好適には、過硫酸カリウム、過硫酸ナトリウ
ム、アンモニウムセリウムナイトレイト(CAN) 、2,3-ジ
クロロ-5,6- ジシアノ-p- ベンゾキノン(DDQ) が用いら
れる。The reduction catalyst used in the catalytic reduction is not particularly limited as long as it is usually used in the catalytic reduction reaction, but preferably palladium carbon,
Raney-nickel, platinum oxide, platinum black, rhodium-aluminum oxide, triphenylphosphine-rhodium chloride,
Palladium-barium sulfate is used. The pressure is not particularly limited, but is usually 1 to 10 atm. The reaction temperature and the reaction time will differ depending on the types of starting materials, solvents, catalysts, etc., but are usually 0 to 100 ° C. and 5 minutes to 2
It is carried out for 4 hours. The solvent used for removal by oxidation is not particularly limited as long as it does not participate in this reaction, but a water-containing organic solvent is preferable. Preferable examples of such an organic solvent include ketones such as acetone, methylene chloride, chloroform, halogenated hydrocarbons such as carbon tetrachloride, nitriles such as acetonitrile, diethyl ether, tetrahydrofuran and dioxane. Ethers, dimethylformamide,
Mention may be made of amides such as dimethylacetamide, hexamethylphosphorotriamide and sulfoxides such as dimethylsulfoxide. The oxidizing agent used is not particularly limited as long as it is a compound used for oxidation, but preferably potassium persulfate, sodium persulfate, ammonium cerium nitrate (CAN), 2,3-dichloro-5. , 6-Dicyano-p-benzoquinone (DDQ) is used.
【０１１７】反応温度及び反応時間は、出発物質、溶媒
及び触媒の種類等により異なるが、通常、０乃至１５０
℃で、１０分乃至２４時間実施される。The reaction temperature and the reaction time vary depending on the starting materials, the solvent, the kind of the catalyst and the like, but are usually 0 to 150.
It is carried out at 0 ° C. for 10 minutes to 24 hours.
【０１１８】又、液体アンモニア中若しくはメタノ−
ル、エタノ−ルのようなアルコ−ル中において、−７８
乃至−２０℃で、金属リチウム、金属ナトリウムのよう
なアルカリ金属類を作用させることによっても除去でき
る。In liquid ammonia or methanol
-78 in alcohols such as alcohol and ethanol
It can also be removed by reacting an alkali metal such as metallic lithium or metallic sodium at from -20 ° C.
【０１１９】更に、溶媒中、塩化アルミニウム−沃化ナ
トリウム、又はトリメチルシリルイオダイドのようなア
ルキルシリルハライド類を用いても除去することができ
る。使用される溶剤としては、本反応に関与しないもの
であれば特に限定はないが、好適には、アセトニトリル
のようなニトリル類、メチレンクロリド、クロロホルム
のようなハロゲン化炭化水素類又はこれらの混合溶剤が
使用される。反応温度及び反応時間は、出発物質、溶媒
等により異なるが、通常は０乃至５０℃で、５分乃至３
日間実施される。Further, it can be removed by using aluminum chloride-sodium iodide or alkylsilyl halides such as trimethylsilyl iodide in a solvent. The solvent used is not particularly limited as long as it does not participate in the reaction, but preferably, nitriles such as acetonitrile, methylene chloride, halogenated hydrocarbons such as chloroform or a mixed solvent thereof. Is used. The reaction temperature and the reaction time will differ depending on the starting materials, solvent, etc., but are usually 0 to 50 ° C., and 5 minutes to 3 minutes.
It is carried out for a day.
【０１２０】尚、反応基質が硫黄原子を有する場合は、
好適には、塩化アルミニウム−沃化ナトリウムが用いら
れる。When the reaction substrate has a sulfur atom,
Aluminum chloride-sodium iodide is preferably used.
【０１２１】例えば、反応混合物を適宜中和し、又、不
溶物が存在する場合には濾過により除去した後、水と酢
酸エチルのような混和しない有機溶媒を加え、水洗後、
目的化合物を含む有機層を分離し、無水硫酸マグネシウ
ム等で乾燥後、溶剤を留去することによって得られる。For example, the reaction mixture is appropriately neutralized, and if insoluble matter is removed by filtration, water and an immiscible organic solvent such as ethyl acetate are added, followed by washing with water,
The organic layer containing the target compound is separated, dried over anhydrous magnesium sulfate or the like, and then the solvent is distilled off.
【０１２２】得られた目的化合物は必要ならば、常法、
例えば再結晶、再沈殿又はクロマトグラフィー等によっ
て更に精製できる。If necessary, the obtained target compound can be obtained by a conventional method,
It can be further purified by, for example, recrystallization, reprecipitation or chromatography.
【０１２３】（第７，１２，１４，１７，２３，２６，
２８，３０，３３，３５工程）本工程は前記有効なる配
列の３’末端側のヌクレオシドを担持したＣＰＧをＤＮ
Ａ合成機上で、一般的にＤＮＡ鎖の伸長反応に用いられ
る操作をくりかえし、前記有効なる配列の５’末端の−
ヌクレオチド前までを合成させて、ＣＰＧに担持された
状態で、一個以上のリン酸トリエステル基がチオリン酸
トリエステル基、メチルホスホネート基あるいはメトキ
シエチルアミノホスフェート基で変換されているオリゴ
デオキシリボヌクレオチド（３）等を得る工程である。
次にＤＮＡ合成機上でのＤＮＡ鎖の伸長反応に関して、
ホスホロアミダイド法、メチルホスホネートアミダイト
法及びホスホン酸法について述べるが、この方法に限定
されるわけではない。(7th, 12th, 14th, 17th, 23rd, 26th,
28, 30, 33, 35) In this step, the CPG carrying the nucleoside at the 3'-terminal side of the effective sequence is DN
On the A synthesizer, the operation generally used for the elongation reaction of the DNA chain is repeated, and the 5'-end of the effective sequence is
Oligodeoxyribonucleotides (3) in which one or more phosphate triester groups are converted by a thiophosphate triester group, a methylphosphonate group or a methoxyethylaminophosphate group in a state of being supported on CPG by synthesizing up to nucleotides before (3 ) And the like.
Next, regarding the elongation reaction of the DNA chain on the DNA synthesizer,
The phosphoramidide method, the methylphosphonate amidite method and the phosphonic acid method are described, but the method is not limited thereto.
【０１２４】第７工程において、リン酸トリエステル結
合を形成させる場合は、市販されているＤ''担持ＣＰＧ
（３−１）をＤＮＡ合成機上で５’−末端のＤＭＴ基を
脱ＤＭＴ化試薬を用いて除去した後、ＤＮＡ合成機用と
して市販されているヌクレオシドホスホロアミダイト試
薬を用いて縮合させ、亜リン酸トリエステル結合を形成
させて、適当な酸化剤を用いてリン酸トリエステルにま
で酸化する。また、チオリン酸トリエステル結合を形成
させる場合は、リン酸トリエステル結合を形成させた場
合と同様に亜リン酸トリエステル結合を形成させて、適
当なチオエート化試薬を反応させるか、あるいは、ＤＮ
Ａ合成機用として市販されているヌクレオシドホスホン
酸モノエステル（例えば、ミリジェン／バイオサーチよ
り発表されている）を縮合剤と脱酸剤を存在下に脱ＤＭ
Ｔ化したＣＰＧ（３−１）に反応させた後、適当なチオ
エート化試薬と反応させる。また、メチルホスホネート
基を導入する場合は市販されているヌクレオシドメチル
ホスホンアミダイト（例えば、Glen Research より販売
されている）を、テトラゾール等の酸性物質を触媒とし
て反応させた後適当な酸化剤を用いてメチルホスホネー
ト基とする。また、メトキシエチルアミノホスフェート
基を導入する場合は、ＤＮＡ合成機用として市販されて
いるヌクレオシドホスホン酸モノエステルを縮合剤と脱
酸剤を存在下脱ＤＭＴ化したＣＰＧ（３−１）に反応さ
せた後、メトキシエチルアミンを四塩化炭素中で反応さ
せることによりメトキシエチルアミノホスフェート基を
導入する。これらの操作のいずれかを行い、前記有効な
配列の一ヌクレオチド前までを合成して、ＤＭＴ基を
５’−末端に有するＣＰＧに担持されたＯＤＮ（３）
（オリゴデオキシヌクレオチド）を得る。In the seventh step, when a phosphate triester bond is formed, a commercially available D ″ -supporting CPG is used.
(3-1) after removing the DMT group of the 5'-terminal on the DNA synthesizer using a de-DMT-removing reagent, it is condensed using a commercially available nucleoside phosphoramidite reagent for a DNA synthesizer, The phosphite triester bond is formed and oxidized to phosphotriester using a suitable oxidant. When a thiophosphoric acid triester bond is formed, a phosphite triester bond is formed in the same manner as in the case where the phosphoric acid triester bond is formed and reacted with an appropriate thioate-forming reagent, or DN
A Decomposition of commercially available nucleoside phosphonic acid monoester for synthesizer (for example, announced by Milligen / Biosearch) in the presence of a condensing agent and a deoxidizing agent.
After reacting with TPG-modified CPG (3-1), it is reacted with an appropriate thioating reagent. When introducing a methylphosphonate group, a commercially available nucleoside methylphosphonamidite (for example, sold by Glen Research) is reacted with an acidic substance such as tetrazole as a catalyst and then methylated with an appropriate oxidizing agent. Phosphonate group. When a methoxyethylaminophosphate group is introduced, a commercially available nucleoside phosphonic acid monoester for a DNA synthesizer is reacted with decondensed CPG (3-1) in the presence of a condensing agent and a deoxidizing agent. Afterwards, the methoxyethylaminophosphate group is introduced by reacting methoxyethylamine in carbon tetrachloride. Performing any of these operations, synthesizing up to one nucleotide before the effective sequence, and carrying out ODN (3) carried on CPG having a DMT group at the 5'-end.
(Oligodeoxynucleotide) is obtained.
【０１２５】５’−末端がＤＭＴ基で保護された、所望
のヌクレオチド配列のＯＤＮを担持したＣＰＧはＤＮＡ
合成機、たとえばアプライドバイオシステムズ社のホス
ホロアミダイト法によるモデル３８０Ｂや、ミリジエン
／バイオサーチのホスホロアミダイト法によるサイクロ
ンプラスなどを用いてＮｕｃｌｅｉｃ ＡｃｉｄｓＲｅ
ｓ，１２ ４５３９（１９８４）における方法、あるい
はその変法によって合成し得る。CPG carrying ODN of the desired nucleotide sequence, protected at the 5'-end with a DMT group, is DNA
Nucleic Acids Re using a synthesizer, for example, Model 380B by the phosphoramidite method of Applied Biosystems, or Cyclone Plus by the phosphoramidite method of Millidiene / Biosearch
s, 12 4539 (1984), or a modification thereof.
【０１２６】また、ODN の合成の材料に用いるヌクレオ
チドユニットの塩基部としては、アシル基で保護された
ものを用いる。アシル基としては、塩基部がＡ、Ｃの場
合はベンゾイル基がＧの場合はイソブチリル基が好適に
用いられる。As the base portion of the nucleotide unit used as the material for the synthesis of ODN, one that is protected by an acyl group is used. As the acyl group, an isobutyryl group is preferably used when the base moiety is A and C and a benzoyl group is G.
【０１２７】本工程のヌクレオシドホスホロアミダイト
試薬及びヌクレオシドメチルホスホンアミダイト試薬を
用いた縮合反応において触媒として使用される酸性物質
としては、テトラゾール等の酸性物質があげられるが、
好適には、テトラゾールである。Examples of the acidic substance used as a catalyst in the condensation reaction using the nucleoside phosphoramidite reagent and the nucleoside methylphosphonamidite reagent in this step include tetrazole and other acidic substances.
Preferred is tetrazole.
【０１２８】使用される溶剤としては、反応を阻害しな
いものであれば特に限定はしないが、アセトニトリル及
びテトラヒドロフランが好適である。The solvent used is not particularly limited as long as it does not inhibit the reaction, but acetonitrile and tetrahydrofuran are preferred.
【０１２９】反応温度は、−３０〜５０℃までのいずれ
でもよいが、通常は、室温で実施する。The reaction temperature may be anywhere from -30 to 50 ° C, but it is usually carried out at room temperature.
【０１３０】反応時間は、１分から２０時間まで反応温
度によって異なるが、室温で反応を実施した場合は、１
０分間で反応は終了する。The reaction time varies depending on the reaction temperature from 1 minute to 20 hours, but when the reaction is carried out at room temperature, it is 1
The reaction is completed in 0 minutes.
【０１３１】本工程の酸化反応において使用される酸化
剤としては、通常、酸化反応に使用されるものであれば
特に限定はないが、好適には、過マンガン酸カリウム、
二酸化マンガンのような酸化マンガン類；四酸化ルテニ
ウムのような酸化ルテニウム類；二酸化ゼレンのような
ゼレン化合物；塩化鉄のような鉄化合物：四酸化オスミ
ウムのようなオスミウム化合物；酸化銀のような銀化合
物；酢酸水銀のような水銀化合物、酸化鉛、四酸化鉛の
ような酸化鉛化合物；クロム酸カリウム、クロム酸−硫
酸錯体、クロム酸−ピリジン錯体のようなクロム酸化合
物、セリウムアンモニウムナイトレイト(CAN) のような
セリウム化合物等の無機金属酸化剤；塩素分子、臭素分
子、沃素分子のようなハロゲン分子；過沃素酸ナトリウ
ムのような過沃素酸類；オゾン；過酸化水素水；亜硝酸
のような亜硝酸化合物；亜塩素酸カリウム、亜塩素酸ナ
トリウムのような亜塩素酸化合物；過硫酸カリウム、過
硫酸ナトリウムのような亜塩素酸化合物；過硫酸カリウ
ム、過硫酸ナトリウムのような過硫酸化合物等の無機酸
化剤；DMSO酸化に使用される試薬類（ジメチルスルホキ
シドとジシクロヘキシルカルボジイミド、オキザリルク
ロリド、無水酢酸若しくは五酸化燐との錯体又はピリジ
ン−無水硫酸の錯体）；t-ブチルヒドロパーオキシドの
ようなパーオキシド類；トリフェニルメチルカチオンの
ような安定なカチオン類；N-ブロモコハク酸イミドのよ
うなコハク酸イミド類、次亜塩素酸t-ブチルのような次
亜塩素酸化合物；アゾジカルボン酸エステルのようなア
ゾジカルボン酸化合物；ジメチルジスルフィド、ジフェ
ニルジスルフィド、ジピリジルジスルフィドのようなジ
スルフィド類とトリフェニルホスフィン；亜硝酸メチル
のような亜硝酸エステル類；四臭化メタンのようなテト
ラハロゲン化炭素、2,3-ジクロロ-5,6- ジシアノ-p- ベ
ンゾキノン(DDQ) のようなキノン化合物等の有機酸化剤
を挙げることができ、好適にはヨードである。The oxidizing agent used in the oxidation reaction of this step is not particularly limited as long as it is usually used in the oxidation reaction, but preferably potassium permanganate,
Manganese oxides such as manganese dioxide; Ruthenium oxides such as ruthenium tetroxide; Zelene compounds such as selene dioxide; Iron compounds such as iron chloride: Osmium compounds such as osmium tetroxide; Silver such as silver oxide Compounds: mercury compounds such as mercury acetate, lead oxide compounds such as lead oxide and lead tetraoxide; potassium chromate, chromic acid compounds such as chromic acid-sulfuric acid complex, chromic acid-pyridine complex, cerium ammonium nitrate ( Inorganic metal oxidizers such as cerium compounds such as CAN); halogen molecules such as chlorine molecules, bromine molecules, iodine molecules; periodic acids such as sodium periodate; ozone; hydrogen peroxide solution; Nitrous acid compounds; chlorite compounds such as potassium chlorite and sodium chlorite; potassium persulfate and sodium persulfate Chlorous acid compounds; inorganic oxidizers such as persulfate compounds such as potassium persulfate and sodium persulfate; reagents used for DMSO oxidation (dimethyl sulfoxide and dicyclohexylcarbodiimide, oxalyl chloride, acetic anhydride or phosphorus pentoxide) Or pyridine-sulfuric anhydride complex); peroxides such as t-butyl hydroperoxide; stable cations such as the triphenylmethyl cation; succinimides such as N-bromosuccinimide, Hypochlorous acid compounds such as t-butyl chlorite; azodicarboxylic acid compounds such as azodicarboxylic acid esters; disulfides such as dimethyl disulfide, diphenyl disulfide, dipyridyl disulfide and triphenylphosphine; such as methyl nitrite Nitrites; methane tetrabromide Tetra halocarbon such as 2,3-dichloro-5,6-dicyano -p- benzoquinone can be mentioned organic oxidizing agent of quinone compounds such as (DDQ), preferably iodo.
【０１３２】使用される溶剤としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、ベンゼン、トルエン、キシレンの
ような芳香族炭化水素類；メチレンクロリド、クロロホ
ルムのようなハロゲン化炭化水素類；エーテル、テトラ
ヒドロフラン、ジオキサン、ジメトキシエタンのような
エーテル類；ジメチルホルムアミド、ジメチルアセトア
ミド、ヘキサメチルホスホロトリアミドのようなアミド
類；ジメチルスルホキシドのようなスルホキシド類；メ
タノール、エタノール、n-プロパノール、イソプロパノ
ール、n-ブタノール、イソブタノール、イソアミルアル
コールのようなアルコール類；硫酸水のような希釈酸；
水酸化ナトリウム水のような希釈塩基；水；アセトン；
メチルエチルケトンのようなケトン類；ピリジンのよう
な複素環アミン類又はアセトニトリルのようなニトリル
類をあげることができ、好適には、複素環アミン類（ピ
リジン）、ニトリル類（特にアセトニトリル）、エーテ
ル類（特にテトラヒドロフラン）、ハロゲン化炭化水素
類（特にメチレンクロリド）である。The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably, aromatic hydrocarbons such as benzene, toluene and xylene; Halogenated hydrocarbons such as methylene chloride, chloroform; ethers such as ether, tetrahydrofuran, dioxane, dimethoxyethane; amides such as dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide; sulfoxides such as dimethylsulfoxide Alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, isoamyl alcohol; dilute acids such as sulfuric acid;
Dilute base such as sodium hydroxide water; water; acetone;
Mention may be made of ketones such as methyl ethyl ketone; heterocyclic amines such as pyridine or nitriles such as acetonitrile, preferably heterocyclic amines (pyridine), nitriles (particularly acetonitrile), ethers ( In particular, tetrahydrofuran) and halogenated hydrocarbons (especially methylene chloride).
【０１３３】反応温度は−５０乃至100 ℃で行なわれ、
反応時間は、主に反応温度、原料化合物又は使用される
溶媒の種類によって異なるが、通常３０分乃至１５時間
である。尚、上記酸化反応においては、トリエチルベン
ジルアンモニウムクロライド、トリブチルベンジルアン
モニウムブロミドのような層間移動触媒を加えることに
よって反応が加速される。The reaction temperature is -50 to 100 ° C, and
The reaction time varies depending mainly on the reaction temperature, the starting compound or the type of solvent used, but it is usually 30 minutes to 15 hours. In the above oxidation reaction, the reaction is accelerated by adding an interlayer transfer catalyst such as triethylbenzylammonium chloride or tributylbenzylammonium bromide.
【０１３４】チオエート化の試薬としては３価のリンに
反応してチオエートを形成する事の出来る試薬であれば
特に限定はされないが、硫黄のほかアプライドバイオシ
ステムズ社より発売されているテトラエチルチウラムジ
スルフィド（ＴＥＴＤ）やミリジェン／バイオリサーチ
より発売されているＢｅａｕｃａｇｅ試薬などが好適で
あり、前者の場合はＴｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔ
ｅｒｓ ３２，３００５（１９９１）に示された方法あ
るいはその変法に従って処理し、後者の場合はJ.Am.Che
m.Soc.１１２ １２５３（１９９０）に示された方法あ
るいはその変法に従って処理することによってチオリン
酸トリエステル基を得ることが出来る。ヌクレオシドホ
スホン酸モノエステルを用いた縮合反応において用いら
れる縮合剤としてはホスホン酸モノエステルと混合酸無
水物を形成するものであれば特に限定はないが好適には
アダマンタン−１−カルボニルクロリドやピバロイルク
ロリドが用いられる。脱酸剤としては酸クロリドを用い
てアシル化する際に用いられる脱酸剤であれば特に限定
はないが通常はピリジンのような芳香族アミンが用いら
れる。触媒としては特に反応を阻害しなければ限定はな
いが、好適には無水のアセトニトリルのようなニトリル
類が用いられる。反応時間は室温で反応を実施する場合
は５〜６０分である。The thioating reagent is not particularly limited as long as it is a reagent capable of reacting with trivalent phosphorus to form a thioate, but in addition to sulfur, tetraethylthiuram disulfide (sold by Applied Biosystems) ( TETD) and Beaucage reagent released by Milligen / Bioresearch are suitable, and in the former case, Tetrahedron Lett
ers 32 , 3005 (1991) or a modification thereof, in the latter case J. Am. Che
The thiophosphoric acid triester group can be obtained by treatment according to the method shown in m.Soc. 112 1253 (1990) or its modification. The condensing agent used in the condensation reaction using the nucleoside phosphonic acid monoester is not particularly limited as long as it forms a mixed acid anhydride with the phosphonic acid monoester, but is preferably adamantane-1-carbonyl chloride or pivalo. Ilchloride is used. The deoxidizing agent is not particularly limited as long as it is a deoxidizing agent used when acylating with an acid chloride, but an aromatic amine such as pyridine is usually used. The catalyst is not particularly limited as long as it does not inhibit the reaction, but nitriles such as anhydrous acetonitrile are preferably used. The reaction time is 5 to 60 minutes when the reaction is carried out at room temperature.
【０１３５】メトキシエチルアミノホスフェート基を形
成させる反応においての溶媒としては反応を阻害しなけ
れば特に限定はないが、通常は試薬である四塩化炭素を
溶媒量で用いる。The solvent in the reaction for forming the methoxyethylaminophosphate group is not particularly limited as long as it does not inhibit the reaction, but carbon tetrachloride which is a reagent is usually used in a solvent amount.
【０１３６】反応温度は−５０℃から１００℃まで特に
限定はないが、室温で反応させる場合は反応時間は１〜
１０時間である。The reaction temperature is not particularly limited from -50 ° C to 100 ° C, but when the reaction is carried out at room temperature, the reaction time is from 1 to 1.
10 hours.
【０１３７】第１２、１４、１５、１７、２３、２６、
２８、３０、３３及び３５工程においても、上記に示し
た方法と同様にして行うことができる。12th, 14th, 15th, 17th, 23rd, 26th,
The steps 28, 30, 33 and 35 can be performed in the same manner as the above-mentioned method.
【０１３８】（第９，２０工程）本工程は化合物（４−
２）又は（６−２）遊離の水酸基に無水コハク酸のよう
なジカルボン酸の無水物を塩基性触媒の存在下に反応さ
せる事により、ジカルボン酸のハーフエステルを得る工
程である。(Steps 9 and 20) This step is carried out by using the compound (4-
2) or (6-2) is a step of obtaining a half ester of dicarboxylic acid by reacting a free hydroxyl group with an anhydride of dicarboxylic acid such as succinic anhydride in the presence of a basic catalyst.
【０１３９】用いられるジカルボン酸としては特に限定
はないが、炭素数２〜１０ぐらいまでが好ましく、最も
好ましくはコハク酸、あるいはグルタール酸である。用
いられる塩基性触媒としては、ジメチルアミノピリジン
やピロリジノピリジンのようなアミノピリジン類、トリ
メチルアミンやトリエチルアミンのような三級アミン、
炭酸水素ナトリウム、炭酸カリウムのようなアルカリ金
属の炭酸塩などが好ましいが、ジメチルアミノピリジン
や、ピロリジノピリジンが最も好ましい。The dicarboxylic acid used is not particularly limited, but preferably has about 2 to 10 carbon atoms, and most preferably succinic acid or glutaric acid. As the basic catalyst used, aminopyridines such as dimethylaminopyridine and pyrrolidinopyridine, tertiary amines such as trimethylamine and triethylamine,
Alkali metal carbonates such as sodium hydrogen carbonate and potassium carbonate are preferable, but dimethylaminopyridine and pyrrolidinopyridine are most preferable.
【０１４０】使用される溶剤としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、ベンゼン、トルエン、キシレンの
ような芳香族炭化水素類；メチレンクロリド、クロロホ
ルムのようなハロゲン化炭化水素類；エーテル、テトラ
ヒドロフラン、ジオキサン、ジメトキシエタンのような
エーテル類；ジメチルホルムアミド、ジメチルアセトア
ミド、ヘキサメチルホスホロトリアミドのようなアミド
類；ジメチルスルホキシドのようなスルホキシド類；メ
タノール、エタノール、n-プロパノール、イソプロパノ
ール、n-ブタノール、イソブタノール、イソアミルアル
コールのようなアルコール類；硫酸水のような希釈酸；
水酸化ナトリウム水のような希釈塩基；水；アセトン；
メチルエチルケトンのようなケトン類；ピリジンのよう
な複素環アミン類又はアセトニトリルのようなニトリル
類をあげることができ、好適には、ニトリル類（特にア
セトニトリル）、エーテル類（特にテトラヒドロフラ
ン）、ハロゲン化炭化水素類（特にメチレンクロリド）
である。The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably, aromatic hydrocarbons such as benzene, toluene and xylene; Halogenated hydrocarbons such as methylene chloride, chloroform; ethers such as ether, tetrahydrofuran, dioxane, dimethoxyethane; amides such as dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide; sulfoxides such as dimethylsulfoxide Alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, isoamyl alcohol; dilute acids such as sulfuric acid;
Dilute base such as sodium hydroxide water; water; acetone;
Mention may be made of ketones such as methyl ethyl ketone; heterocyclic amines such as pyridine or nitriles such as acetonitrile, preferably nitriles (especially acetonitrile), ethers (especially tetrahydrofuran), halogenated hydrocarbons. Class (especially methylene chloride)
Is.
【０１４１】反応温度は−５０乃至100 ℃で行なわれ、
反応時間は、主に反応温度、原料化合物又は使用される
溶媒の種類によって異なるが、通常３０分乃至１５時間
である。The reaction temperature is -50 to 100 ° C, and
The reaction time varies depending mainly on the reaction temperature, the starting compound or the type of solvent used, but it is usually 30 minutes to 15 hours.
【０１４２】（第１０，２１工程）本工程は第９又は２
０工程で得られたコハク酸のハーフエステル（４−３）
又は（６−４）をペンタクロルフェノールのようなフェ
ノール類と縮合剤を反応させて活性エステルを形成さ
せ、次にアミノ−ＣＰＧ（４−４）又は（６−５）を塩
基の存在下に反応させて、目的物である（４−５）又は
（６−６）を得る工程である。(10th and 21st steps) This step is the 9th or 2nd step.
Half ester of succinic acid obtained in Step 0 (4-3)
Alternatively, (6-4) is reacted with a phenol such as pentachlorophenol and a condensing agent to form an active ester, and then amino-CPG (4-4) or (6-5) is added in the presence of a base. This is a step of reacting to obtain the desired product (4-5) or (6-6).
【０１４３】使用されるフェノール類としてはカルボン
酸と反応して活性エステルを形成するものであれば特に
限定はないが、ペンタクロロフェノールや４−ニトロフ
ェノールが好適である。The phenols used are not particularly limited as long as they react with a carboxylic acid to form an active ester, but pentachlorophenol and 4-nitrophenol are preferred.
【０１４４】使用される溶剤としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、ジメチルホルムアミド、ジメチルアセトアミ
ド、ヘキサメチルホスホロトリアミドのようなアミド
類；ジメチルスルホキシドのようなスルホキシド類；ア
セトン；メチルエチルケトンのようなケトン類；ピリジ
ンのような複素環アミン又はアセトニトリルのようなニ
トリル類をあげることができ、好適には、ジメチルホル
ムアミドのようなアミド類である。The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but amides such as dimethylformamide, dimethylacetamide and hexamethylphosphorotriamide; dimethyl; Mention may be made of sulfoxides such as sulfoxides; acetone; ketones such as methyl ethyl ketone; heterocyclic amines such as pyridine or nitriles such as acetonitrile, with preference given to amides such as dimethylformamide.
【０１４５】使用される塩基としては、通常の反応にお
いて塩基として使用されるものであれば、特に限定はな
いが、好適にはトリエチルアミン、トリブチルアミン、
ジイソプロピルエチルアミン、Ｎ−メチルモルホリンピ
リジン、４−（Ｎ、Ｎ−ジメチルアミノ）ピリジン、
Ｎ、Ｎ−ジメチルアニリン、Ｎ、Ｎ−ジエチルアニリ
ン、１、５−ジアザビシクロ［４，３，０］ノナ−５−
エン、１、４−ジアザビシクロ［２，２，２］オクタン
（ＤＡＢＣＯ）、１，８−ジアザビシクロ［５，４，
０］ウンデク−７−エン（ＤＢＵ）のような有機塩基類
があげられ、好適には、有機塩基類、特にトリエチルア
ミン、ピリジン、Ｎ−メチルモルホリン、ＤＢＵであ
る。The base used is not particularly limited as long as it is used as a base in a usual reaction, but preferably triethylamine, tributylamine,
Diisopropylethylamine, N-methylmorpholine pyridine, 4- (N, N-dimethylamino) pyridine,
N, N-dimethylaniline, N, N-diethylaniline, 1,5-diazabicyclo [4,3,0] non-5-
Ene, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,8-diazabicyclo [5,4,4]
[0] Organic bases such as [0] undec-7-ene (DBU) are preferred, and organic bases, particularly triethylamine, pyridine, N-methylmorpholine and DBU are preferred.
【０１４６】反応温度は−５０乃至１００℃で行われ、
反応時間は、主に反応温度、原料化合物又は使用される
溶媒の種類によって異なるが、通常反応を室温で行う場
合には３０乃至５０時間である。The reaction temperature is -50 to 100 ° C.,
The reaction time mainly depends on the reaction temperature, the starting compound or the type of solvent used, but it is usually 30 to 50 hours when the reaction is carried out at room temperature.
【０１４７】（第１３，３２工程）第１３工程は、第１
１工程で得られた（４−６）にＤＮＡ合成機上で市販さ
れている５’−Ｏ−ＤＭＴ−ヌクレオシド−３’−ホス
ホロアミダイト試薬を反応させた後、チオエート化試薬
を反応させてチオエート結合を有するＣＰＧ担体である
（４−７）を得る工程である。(13th and 32nd Steps) The 13th step is the first step.
(4-6) obtained in 1 step was reacted with a commercially available 5'-O-DMT-nucleoside-3'-phosphoramidite reagent on a DNA synthesizer, and then with a thioate reagent. It is a step of obtaining (4-7) which is a CPG carrier having a thioate bond.
【０１４８】化合物（６−３’）のＶとしては、第３９
工程においてリン酸エステル結合を形成した後に除去で
きる基であればいずれでもよいが、メトキシ基等の低級
アルキルオキシ基、シアノエチルオキシ基等のシアノア
ルキルオキシ基が好適に用いられる。V of the compound (6-3 ′) is as follows:
Any group may be used as long as it can be removed after forming a phosphate bond in the step, but a lower alkyloxy group such as a methoxy group and a cyanoalkyloxy group such as a cyanoethyloxy group are preferably used.
【０１４９】チオエート化の試薬としては３価のリンに
反応してチオエートを形成する事の出来る試薬であれば
特に限定はされないが、硫黄のほかアプライドバイオシ
ステムズ社より発売されているテトラエチルチウラムジ
スルフィド（ＴＥＴＤ）やミリジエン／バイオリサーチ
より発売されているＢｅａｕｃａｇｅ試薬などが好適で
あり、前者の場合はＴｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔ
ｅｒｓ ３２，３００５（１９９１）に示された方法あ
るいはその変法に従って処理し、後者の場合はJ.Am.Che
m.Soc.１１２ １２５３（１９９０）に示された方法あ
るいはその変法に従って処理することによってＣＰＧと
チオエート結合を介して前記有効なる配列の３’末端部
分のヌクレオシドと結合した（４−７）を得ることが出
来る。The thioating reagent is not particularly limited as long as it is a reagent capable of reacting with trivalent phosphorus to form a thioate, but in addition to sulfur, tetraethylthiuram disulfide (sold by Applied Biosystems) Tetd) and Beaucage reagent sold by Myridiene / Bioresearch are suitable. In the former case, Tetrahedron Lett
ers 32 , 3005 (1991) or a modification thereof, in the latter case J. Am. Che
(4-7) was linked to the nucleoside at the 3'terminal portion of the effective sequence through a thioate bond with CPG by treating according to the method shown in m.Soc. 112 1253 (1990) or a modification thereof. You can get it.
【０１５０】第３２工程においては、ホスホロアミダイ
ト試薬を反応させた後、通常の処理によってリン酸トリ
エステル結合を有するかあるいは、チオエート化試薬を
反応させてチオエート結合を有するＣＰＧ担体である
（７−７）を得ることができる。In the 32nd step, a CPG carrier having a phosphate triester bond by a usual treatment after reacting with a phosphoramidite reagent or a thioate bond by reacting with a thioate reagent (7) -7) can be obtained.
【０１５１】（第１５工程）本工程は（４−６）と同様
にして得られる、脱ＤＭＴ化された（５−１）に、市販
されているヌクレオシドホスホン酸モノエステル（５−
２）（例えばミリジエン／バイオサーチから発売されて
いる）を縮合剤と脱酸剤の存在下に反応させてホスホン
酸のジエステルを結合したＣＰＧ（５−３）を得る工程
である。用いられる縮合剤としてはホスホン酸モノエス
テルと混合酸無水物を形成するものであれば特に限定は
ないが好適にはアダマンタン−１−カルボニルクロリド
やピバロイルクロリドが用いられる。脱酸剤としては酸
クロリドを用いてアシル化する際に用いられる脱酸剤で
あれば特に限定はないが通常はピリジンのような芳香族
アミンが用いられる。溶媒としては特に反応を阻害しな
ければ限定はないが、好適には無水のアセトニトリルの
ようなニトリル類が用いられる。反応時間は室温で反応
を実施する場合は５〜６０分である。(Step 15) In this step, the de-DMT-ized (5-1) obtained in the same manner as in (4-6) was added to the commercially available nucleoside phosphonic acid monoester (5-).
2) A step of reacting (for example, sold by Myridiene / Biosearch) in the presence of a condensing agent and a deoxidizing agent to obtain CPG (5-3) having a diester of phosphonic acid bonded thereto. The condensing agent used is not particularly limited as long as it forms a mixed acid anhydride with a phosphonic acid monoester, but adamantane-1-carbonyl chloride or pivaloyl chloride is preferably used. The deoxidizing agent is not particularly limited as long as it is a deoxidizing agent used when acylating with an acid chloride, but an aromatic amine such as pyridine is usually used. The solvent is not particularly limited as long as it does not inhibit the reaction, but nitriles such as anhydrous acetonitrile are preferably used. The reaction time is 5 to 60 minutes when the reaction is carried out at room temperature.
【０１５２】（第１６工程）本工程はホスホン酸ジエス
テル結合を有するＣＰＧ（５−３）にアルキルアミン及
び四塩化炭素を反応させることにより、ホスホロアミデ
ート結合を形成させる工程である。アルキルアミンとし
ては所望のアルキルアミンを用い、溶媒としては反応を
阻害しなければ特に限定はないが、通常は試薬である四
塩化炭素を溶媒量で用いる。(Step 16) In this step, CPG (5-3) having a phosphonate diester bond is reacted with alkylamine and carbon tetrachloride to form a phosphoramidate bond. A desired alkylamine is used as the alkylamine, and the solvent is not particularly limited as long as it does not inhibit the reaction, but carbon tetrachloride, which is a reagent, is usually used in a solvent amount.
【０１５３】反応温度は−５０°から１００℃まで特に
限定はないが、室温で反応させる場合は反応時間は１〜
１０時間である。The reaction temperature is not particularly limited from -50 ° to 100 ° C, but when the reaction is carried out at room temperature, the reaction time is 1 to
10 hours.
【０１５４】（第１９、３６工程）本工程は、不活性溶
剤中、脱酸剤の存在下、化合物（２）又は（６−２）
に、３価のリン酸化剤であるクロロホスホロアミダイト
（６−３’）を反応させて、３’亜リン酸誘導体（３）
又は（６−３）を製造する工程である。(Steps 19 and 36) In this step, compound (2) or (6-2) was added in the presence of a deoxidizing agent in an inert solvent.
And a chlorophosphoramidite (6-3 ′), which is a trivalent phosphorylating agent, are reacted with the 3 ′ phosphorous acid derivative (3)
Alternatively, it is a step of producing (6-3).
【０１５５】化合物（６−３’）のＵとしては、ジメチ
ルアミノ基、ジイソプロピルアミノ基等のジアルキルア
ミノ基、モルホリノ基等の１又は２個の酸素原子及び／
又は窒素原子を環内に有する複素環基などが用いられ
る。As U of the compound (6-3 ′), dialkylamino group such as dimethylamino group and diisopropylamino group, 1 or 2 oxygen atoms such as morpholino group and / or
Alternatively, a heterocyclic group having a nitrogen atom in the ring is used.
【０１５６】化合物（６−３’）のＶとしては、第３９
工程においてリン酸エステル結合を形成した後に除去で
きる基であればいずれでもよいが、メトキシ基等の低級
アルキルオキシ基、シアノエチルオキシ基等のシアノア
ルキルオキシ基が好適に用いられる。化合物（６−
３’）としては、クロロモルホリノメトキシホスフィ
ン、クロロモルホリノシアノエトキシホスフィン、クロ
ロジメチルアミノメトキシホスフィン、クロロジメチル
アミノシアノエトキシホスフィン、クロロジイソプロピ
ルアミノメトキシホスフィン、クロロジイソプロピルア
ミノシアノエトキシホスフィンのようなホスフィン類が
あげられ、好適には、クロロモルホリノメトキシホスフ
ィン、クロロモルホリノシアノエトキシホスフィン、ク
ロロジイソプロピルアミノメトキシホスフィン、クロロ
ジイソプロピルアミノシアノエトキシホスフィンであ
る。V of the compound (6-3 ′) is as follows:
Any group may be used as long as it can be removed after forming a phosphate bond in the step, but a lower alkyloxy group such as a methoxy group and a cyanoalkyloxy group such as a cyanoethyloxy group are preferably used. Compound (6-
Examples of 3 ') include phosphines such as chloromorpholinomethoxyphosphine, chloromorpholinocyanoethoxyphosphine, chlorodimethylaminomethoxyphosphine, chlorodimethylaminocyanoethoxyphosphine, chlorodiisopropylaminomethoxyphosphine and chlorodiisopropylaminocyanoethoxyphosphine. Preferred are chloromorpholinomethoxyphosphine, chloromorpholinocyanoethoxyphosphine, chlorodiisopropylaminomethoxyphosphine and chlorodiisopropylaminocyanoethoxyphosphine.
【０１５７】使用される溶剤としては、反応に影響を与
えないものであれば特に限定はないが、好適には、例え
ば、テトラヒドロフラン、ジエチルエーテル、ジオキサ
ンのようなエーテル類である。The solvent used is not particularly limited as long as it does not affect the reaction, but ethers such as tetrahydrofuran, diethyl ether and dioxane are preferred.
【０１５８】使用される脱酸剤としては、ピリジン、ジ
メチルアミノピリジンのような複素環アミン類、トリメ
チルアミン、トリエチルアミン、ジイソプロピルエチル
アミンのような脂肪族アミン類があげられるが、好適に
は脂肪族アミン類（特にジイソプロピルエチルアミン）
である。 反応温度は、特に限定はないが、通常−５０
乃至５０℃であり、好適には室温である。反応時間は、
使用する原料、試薬、温度等により異なるが、通常、５
分から３０時間であり、好適には、室温で反応した場
合、３０分である。 例えば、反応混合物を適宜中和
し、又、不溶物が存在する場合には濾過により除去した
後、水と酢酸エチルのような混和しない有機溶媒を加
え、水洗後、目的化合物を含む有機層を分離し、無水硫
酸マグネシウム等で乾燥後、溶剤を留去することによっ
て得られる。得られた目的化合物は必要ならば、常法、
例えば再結晶、再沈殿又はクロマトグラフィ−等によっ
て更に精製できる。 （第２４工程）本工程は第７工程においてＤＮＡ合成機
用のヌクレオチドユニットのかわりに化合物（６−３）
を反応させる以外は同様に処理してリン酸トリエステル
結合を有するＣＰＧ担体（６−８）を得る工程である。Examples of the deoxidizing agent used include heterocyclic amines such as pyridine and dimethylaminopyridine, and aliphatic amines such as trimethylamine, triethylamine and diisopropylethylamine, and aliphatic amines are preferable. (Especially diisopropylethylamine)
Is. The reaction temperature is not particularly limited, but is usually -50.
To 50 ° C., preferably room temperature. The reaction time is
Usually 5 depending on the raw materials, reagents, temperature, etc. used.
Minutes to 30 hours, preferably 30 minutes when reacted at room temperature. For example, the reaction mixture is appropriately neutralized, and if insolubles are present, they are removed by filtration, water and an immiscible organic solvent such as ethyl acetate are added, and the mixture is washed with water to form an organic layer containing the target compound. It is obtained by separating, drying over anhydrous magnesium sulfate and the like, and distilling off the solvent. If necessary, the obtained target compound is subjected to a conventional method,
It can be further purified by, for example, recrystallization, reprecipitation or chromatography. (24th step) In this step, the compound (6-3) is used instead of the nucleotide unit for the DNA synthesizer in the 7th step.
Is a step of obtaining the CPG carrier (6-8) having a phosphate triester bond by performing the same treatment except reacting.
【０１５９】（第２７，２９工程）本工程は第２５工程
で得られたＣＰＧ担体（６−９）を第２４及び２５工程
と同一の処理を行ない、リン酸トリエステル結合を２個
及び３個有するＣＰＧ担体（６−１０），（６−１１）
を得る工程である。(Steps 27 and 29) In this step, the CPG carrier (6-9) obtained in the 25th step was subjected to the same treatments as those in the 24th and 25th steps to prepare two phosphate triester bonds and three phosphate bonds. CPG carrier (6-10), (6-11)
Is a step of obtaining.
【０１６０】（第３１工程）本工程は市販されているＣ
ＰＧ担体の５’ＤＭＴ基を除去した（７−２）にやはり
市販されている（２−シアノエトキシ）−２−［２’−
Ｏ−（４，４’−ジメトキシトリチルオキシエチルスル
ホニル］エトキシ−Ｎ，Ｎ−ジイソプロピルアミノホス
フィン（７−１）［Ｔｈｏｍａｓ Ｈｏｒｎら、Ｔｅｔ
ｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ ２７，４７０５
（１９８６）を第２４工程と同様の処理を行ない、４，
４’−ジメトキシトリチルオキシエチルスルホニルエト
キシ基を有するＣＰＧ担体（７−３）を得る工程であ
る。(Step 31) This step is commercially available C
(2-Cyanoethoxy) -2- [2'-, which is also commercially available, in (7-2) after removing the 5'DMT group of the PG carrier.
O- (4,4'-dimethoxytrityloxyethylsulfonyl] ethoxy-N, N-diisopropylaminophosphine (7-1) [Thomas Horn et al., Tet.
rhedron Letters 27 , 4705
(1986) is treated in the same manner as the 24th step,
It is a step of obtaining a CPG carrier (7-3) having a 4'-dimethoxytrityloxyethylsulfonylethoxy group.
【０１６１】（第３４工程）本工程は第３１工程で製造
されたＣＰＧ担体（７−３）のＤＭＴ基を除去した後、
（７−４）で示される５’位にＤＭＴ基を有し、３’位
にアルキルリン酸エステル、フェニルリン酸エステルあ
るいはアルキル及びフェニルホスホン酸がエステル結合
したヌクレオチドを縮合剤を用いて反応させＣＰＧ担体
（７−５）を得る工程である。 本工程に用いられる溶
媒は反応を阻害しないものであれば特に限定はないが好
適にはピリジンのような芳香族アミンが用いられる。
縮合に用いられる縮合剤としてはジシクロヘキシルカル
ボジイミド（ＤＣＣ）、メシチレンスルホン酸クロリド
（Ｍｓ−Ｃｌ）、トリイソプロピルベンゼンスルホニル
クロリド、メシチレンスルホン酸トリアゾリド（ＭＳ
Ｔ）、メシチレンスルホン酸−３−ニトロトリアゾリド
（ＭＳＮＴ）、トリイソプロピルベンゼンスルホン酸テ
トラゾリド（ＴＰＳ−Ｔｅ）、トリイソプロピルベンゼ
ンスルホン酸ニトロイミダゾリド（ＴＰＳ−ＮＩ）、及
びトリイソプロピルベンゼンスルホン酸ピリジルテトラ
ゾリドなどをあげる事が出来るが、好適にはＭＳＮＴや
ＴＰＳ−Ｔｅ及びＴＰＳ−ＮＩが用いられる。(Step 34) In this step, after removing the DMT group of the CPG carrier (7-3) produced in the 31st step,
(7-4) having a DMT group at the 5'position and having an alkyl phosphate ester, a phenyl phosphate ester or an alkyl- and phenylphosphonic acid ester-bonded nucleotide at the 3'position are reacted using a condensing agent. It is a step of obtaining a CPG carrier (7-5). The solvent used in this step is not particularly limited as long as it does not inhibit the reaction, but an aromatic amine such as pyridine is preferably used.
Examples of the condensing agent used for condensation include dicyclohexylcarbodiimide (DCC), mesitylenesulfonic acid chloride (Ms-Cl), triisopropylbenzenesulfonyl chloride, mesitylenesulfonic acid triazolide (MS).
T), mesitylenesulfonic acid-3-nitrotriazolide (MSNT), triisopropylbenzenesulfonic acid tetrazolid (TPS-Te), triisopropylbenzenesulfonic acid nitroimidazolide (TPS-NI), and triisopropylbenzenesulfonic acid pyridyl Examples thereof include tetrazolide, but MSNT, TPS-Te and TPS-NI are preferably used.
【０１６２】反応温度は−１０〜１００℃まで特に限定
はないが通常は室温で実施する。反応時間は使用する溶
媒、反応温度によって異なるが、反応溶媒としてピリジ
ンを使用し、室温で実施した場合は３０分である。The reaction temperature is not particularly limited to -10 to 100 ° C, but is usually room temperature. The reaction time varies depending on the solvent used and the reaction temperature, but it is 30 minutes when the reaction is carried out at room temperature using pyridine.
【０１６３】（第３７工程）本工程は第３６工程で得ら
れる化合物（８）と、ＤＮＡ合成機で合成され、ＣＰＧ
に結合したままのＯＤＮ（３），（４ａ〜ｂ），
（５），（６ａ〜ｄ）及び（７ａ〜ｂ）の５’末端のＤ
ＭＴ基のみを除去したＯＤＮを酸触媒を用いて縮合さ
せ、亜リン酸トリエステル結合を形成させて、適当な酸
化剤を用いてリン酸トリエステルに酸化し、あるいは適
当なチオエート化剤を用いてチオリン酸トリエステルと
し、ＣＰＧより切り出し、次に保護基を除去して、精製
操作を経て、最終産物（１）を得る工程である。(Step 37) In this step, compound (8) obtained in step 36 was synthesized with a DNA synthesizer to give CPG.
Bound to ODN (3), (4a-b),
D at the 5'end of (5), (6a-d) and (7a-b)
ODN from which only the MT group has been removed is condensed with an acid catalyst to form a phosphite triester bond, and the phosphite triester is oxidized with an appropriate oxidizing agent, or an appropriate thioating agent is used. Is a thiophosphoric acid triester, which is cleaved from CPG, then the protecting group is removed, and a final product (1) is obtained through a purification operation.
【０１６４】本工程の縮合反応において触媒として使用
される酸性物質としては、テトラゾール等の酸性物質が
あげられ、好適には、テトラゾールである。本工程の酸
化反応において使用される酸化剤としては、通常、酸化
反応に使用されるものであれば特に限定はないが、好適
には、過マンガン酸カリウム、二酸化マンガンのような
酸化マンガン類；四酸化ルテニウムのような酸化ルテニ
ウム類；二酸化ゼレンのようなゼレン化合物；塩化鉄の
ような鉄化合物：四酸化オスミウムのようなオスミウム
化合物；酸化銀のような銀化合物；酢酸水銀のような水
銀化合物、酸化鉛、四酸化鉛のような酸化鉛化合物；ク
ロム酸カリウム、クロム酸−硫酸錯体、クロム酸−ピリ
ジン錯体のようなクロム酸化合物、セリウムアンモニウ
ムナイトレイト(CAN) のようなセリウム化合物等の無機
金属酸化剤；塩素分子、臭素分子、沃素分子のようなハ
ロゲン分子；過沃素酸ナトリウムのような過沃素酸類；
オゾン；過酸化水素水；亜硝酸のような亜硝酸化合物；
亜塩素酸カリウム、亜塩素酸ナトリウムのような亜塩素
酸化合物；過硫酸カリウム、過硫酸ナトリウムのような
亜塩素酸化合物；過硫酸カリウム、過硫酸ナトリウムの
ような過硫酸化合物等の無機酸化剤；DMSO酸化に使用さ
れる試薬類（ジメチルスルホキシドとジシクロヘキシル
カルボジイミド、オキザリルクロリド、無水酢酸若しく
は五酸化燐との錯体又はピリジン−無水硫酸の錯体）；
t-ブチルヒドロパーオキシドのようなパーオキシド類；
トリフェニルメチルカチオンのような安定なカチオン
類；N-ブロモコハク酸イミドのようなコハク酸イミド
類、次亜塩素酸t-ブチルのような次亜塩素酸化合物；ア
ゾジカルボン酸エステルのようなアゾジカルボン酸化合
物；ジメチルジスルフィド、ジフェニルジスルフィド、
ジピリジルジスルフィドのようなジスルフィド類とトリ
フェニルホスフィン；亜硝酸メチルのような亜硝酸エス
テル類；四臭化メタンのようなテトラハロゲン化炭素、
2,3-ジクロロ-5,6- ジシアノ-p- ベンゾキノン(DDQ) の
ようなキノン化合物等の有機酸化剤を挙げることがで
き、好適にはヨードである。Examples of the acidic substance used as a catalyst in the condensation reaction in this step include acidic substances such as tetrazole, and preferably tetrazole. The oxidizing agent used in the oxidation reaction of this step is not particularly limited as long as it is usually used in the oxidation reaction, but preferably manganese oxides such as potassium permanganate and manganese dioxide; Ruthenium oxides such as ruthenium tetroxide; Zelene compounds such as selene dioxide; Iron compounds such as iron chloride: Osmium compounds such as osmium tetroxide; Silver compounds such as silver oxide; Mercury compounds such as mercury acetate Lead oxide compounds such as lead oxide, lead tetroxide; potassium chromate, chromic acid compounds such as chromic acid-sulfuric acid complex, chromic acid-pyridine complex, cerium compounds such as cerium ammonium nitrate (CAN), etc. Inorganic metal oxidizers; Halogen molecules such as chlorine molecules, bromine molecules, iodine molecules; Periodic acids such as sodium periodate;
Ozone; hydrogen peroxide; nitrite compounds such as nitrous acid;
Chlorite compounds such as potassium chlorite and sodium chlorite; Chlorite compounds such as potassium persulfate and sodium persulfate; Inorganic oxidizers such as persulfate compounds such as potassium persulfate and sodium persulfate Reagents used for DMSO oxidation (complexes of dimethyl sulfoxide with dicyclohexylcarbodiimide, oxalyl chloride, acetic anhydride or phosphorus pentoxide or pyridine-sulfuric anhydride complexes);
Peroxides such as t-butyl hydroperoxide;
Stable cations such as triphenylmethyl cation; succinimides such as N-bromosuccinimide, hypochlorite compounds such as t-butyl hypochlorite; azodicarboxylic acids such as azodicarboxylic acid esters Acid compounds; dimethyl disulfide, diphenyl disulfide,
Disulfides such as dipyridyl disulfide and triphenylphosphine; nitrites such as methyl nitrite; tetrahalogenated carbons such as methane tetrabromide,
An organic oxidizing agent such as a quinone compound such as 2,3-dichloro-5,6-dicyano-p-benzoquinone (DDQ) can be mentioned, and iodine is preferable.
【０１６５】使用される溶剤としては、反応を阻害せ
ず、出発物質をある程度溶解するものであれば特に限定
はないが、好適には、ベンゼン、トルエン、キシレンの
ような芳香族炭化水素類；メチレンクロリド、クロロホ
ルムのようなハロゲン化炭化水素類；エーテル、テトラ
ヒドロフラン、ジオキサン、ジメトキシエタンのような
エーテル類；ジメチルホルムアミド、ジメチルアセトア
ミド、ヘキサメチルホスホロトリアミドのようなアミド
類；ジメチルスルホキシドのようなスルホキシド類；メ
タノール、エタノール、n-プロパノール、イソプロパノ
ール、n-ブタノール、イソブタノール、イソアミルアル
コールのようなアルコール類；硫酸水のような希釈酸；
水酸化ナトリウム水のような希釈塩基；水；アセトン；
メチルエチルケトンのようなケトン類；ピリジンのよう
な複素環アミン類又はアセトニトリルのようなニトリル
類をあげることができ、好適には、複素環アミン類（特
にピリジン）、ニトリル類（特にアセトニトリル）、エ
ーテル類（特にテトラヒドロフラン）、ハロゲン化炭化
水素類（特にメチレンクロリド）である。反応温度は−
５０乃至100 ℃で行なわれ、反応時間は、主に反応温
度、原料化合物又は使用される溶媒の種類によって異な
るが、通常３０分乃至１５時間である。尚、上記酸化反
応においては、トリエチルベンジルアンモニウムクロリ
ド、トリブチルベンジルアンモニウムブロミドのような
層間移動触媒を加えることによって反応が加速される。
チオエート化の試薬としては３価のリンに反応してチオ
エートを形成する事の出来る試薬であれば特に限定はさ
れないが、硫黄のほかアプライドバイオシステムズ社よ
り発売されているテトラエチルチウラムジスルフィド
（ＴＥＴＤ）やミリジェン／バイオリサーチより発売さ
れているＢｅａｕｃａｇｅ試薬などが好適であり、前者
の場合はＴｅｔｒａｈｅｄｒｏｎ Ｌｅｔｔｅｒｓ ３
２，３００５（１９９１）に示された方法あるいはその
変法に従って処理し、後者の場合はJ.Am.Chem.Soc.１１
２ １２５３（１９９０）に示された方法あるいはその
変法に従って処理することによってチオリン酸トリエス
テル基を得ることが出来る。The solvent used is not particularly limited as long as it does not inhibit the reaction and dissolves the starting material to some extent, but preferably, aromatic hydrocarbons such as benzene, toluene and xylene; Halogenated hydrocarbons such as methylene chloride, chloroform; ethers such as ether, tetrahydrofuran, dioxane, dimethoxyethane; amides such as dimethylformamide, dimethylacetamide, hexamethylphosphorotriamide; sulfoxides such as dimethylsulfoxide Alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, isoamyl alcohol; dilute acids such as sulfuric acid;
Dilute base such as sodium hydroxide water; water; acetone;
Mention may be made of ketones such as methyl ethyl ketone; heterocyclic amines such as pyridine or nitriles such as acetonitrile, preferably heterocyclic amines (particularly pyridine), nitriles (particularly acetonitrile), ethers. (Especially tetrahydrofuran) and halogenated hydrocarbons (especially methylene chloride). The reaction temperature is −
It is carried out at 50 to 100 ° C., and the reaction time is usually 30 minutes to 15 hours, varying mainly depending on the reaction temperature, the starting compound or the kind of the solvent used. In the above oxidation reaction, the reaction is accelerated by adding an interlayer transfer catalyst such as triethylbenzylammonium chloride or tributylbenzylammonium bromide.
The thioation reagent is not particularly limited as long as it is a reagent capable of reacting with trivalent phosphorus to form a thioate, but in addition to sulfur, tetraethylthiuram disulfide (TETD) sold by Applied Biosystems and Beaucage reagent sold by Milligen / Bioresearch is suitable, and in the former case, Tetrahedron Letters 3
2, 3005 were processed or its variant shown in (1991), in the latter case J.Am.Chem.Soc. 11
The thiophosphoric acid triester group can be obtained by treatment according to the method shown in 212125 (1990) or its modification.
【０１６６】ODN がCPG に結合している場合のCPG より
の切り出し、および、次の５’末端の置換分以外の保護
基の除去は、公知の方法(J.Am.Chem.Soc.,103,3185,(19
81))によって行なうことができる。このようにして得ら
れる、一般式（１）の化合物を含む反応混合物を、逆相
およびイオン交換クロマトグラフィー（高速液体クロマ
トグラフィーを含む。）等の各種クロマトグラフィーな
ど、通常の核酸の精製に用いられる精製操作で精製する
ことにより、前記一般式（１）を有する化合物を得るこ
とができる。Cleavage from CPG in the case where ODN is bound to CPG and removal of a protecting group other than the following 5′-terminal substituent are known methods (J. Am. Chem. Soc., 103). , 3185, (19
81)). The reaction mixture containing the compound of the general formula (1) thus obtained is used for usual nucleic acid purification such as reverse phase and various chromatography such as ion exchange chromatography (including high performance liquid chromatography). The compound having the above-mentioned general formula (1) can be obtained by purification by the purification procedure.
【０１６７】（第３８工程）本工程は不活性溶剤中で化
合物（２）にリン酸化試薬例えばビストリアゾリドを反
応させた後、水を加えて後処理を行ない、中間体となる
モノヌクレオチド（９）を得る工程である。用いられる
溶媒としては反応を阻害しないものであれば特に限定は
ないが通常はピリジンのような芳香族アミンが用いられ
る。リン酸化試薬のＶ基としては、第３９工程の縮合反
応を終了した後塩基部の保護基を除去する条件で除去出
来るものであれば特に限定はないが通常はオルトクロロ
フェノキシ基を用いる。(Step 38) In this step, the compound (2) is reacted with a phosphorylating reagent such as bistriazolide in an inert solvent, and water is added for post-treatment to give an intermediate mononucleotide (9). Is a step of obtaining. The solvent used is not particularly limited as long as it does not inhibit the reaction, but an aromatic amine such as pyridine is usually used. The V group of the phosphorylating reagent is not particularly limited as long as it can be removed under the condition that the protecting group at the base part is removed after completion of the condensation reaction of the 39th step, but an orthochlorophenoxy group is usually used.
【０１６８】反応温度は−２０〜１００℃まで特に限定
はないが通常は室温で実施する。反応時間は用いる溶
媒、反応温度によって異なるが反応溶媒としてピリジン
を用い、室温で実施した場合は一時間である。The reaction temperature is not particularly limited to -20 to 100 ° C, but is usually room temperature. The reaction time varies depending on the solvent used and the reaction temperature, but is 1 hour when the reaction is carried out at room temperature using pyridine as the reaction solvent.
【０１６９】（第３９工程）本工程は第３８工程で得ら
れたモノヌクレオチド（９）とＤＮＡ合成機で合成した
ＯＤＮ（３）、（４ａ）、（４ｂ）、（５）、（６
ａ）、（６ｂ）、（６ｃ）、（６ｄ）、（７ａ）、（７
ｂ）の５´末端のＤＭＴ基のみを除去し、塩基部及びリ
ン酸部分が保護基で保護されたＣＰＧに結合したままの
ＯＤＮを縮合剤を用いて縮合させ、リン酸トリエステル
結合を形成させて、常法に従って、ＣＰＧより切り離
し、次に保護基を除去して、精製操作を経て最終産物
（１）を得る工程である。本工程に用いられる溶媒は反
応を阻害しないものであれば特に限定はないが好適には
ピリジンのような芳香族アミンが用いられる。(Step 39) In this step, the ODNs (3), (4a), (4b), (5) and (6) synthesized with the mononucleotide (9) obtained in the 38th step and a DNA synthesizer were used.
a), (6b), (6c), (6d), (7a), (7
Only the DMT group at the 5'end of b) is removed, and the ODN in which the base portion and the phosphoric acid portion are bonded to the CPG protected with a protecting group is condensed with a condensing agent to form a phosphoric acid triester bond. Then, according to a conventional method, it is a step of cleaving from CPG, then removing a protecting group, and performing a purification operation to obtain the final product (1). The solvent used in this step is not particularly limited as long as it does not inhibit the reaction, but an aromatic amine such as pyridine is preferably used.
【０１７０】縮合に用いられる縮合剤としてはジシクロ
カルボジイミド（ＤＣＣ）、メシチレンスルホン酸クロ
リド（Ｍｓ−Ｃｌ）、トリイソプロピルベンゼンスルホ
ン酸クロリド、メシチレンスルホン酸トリアゾリド（Ｍ
ＳＴ）、メシチレンスルホン酸−３−ニトロトリアゾリ
ド（ＭＳＮＴ）、トリイソプロピルベンゼンスルホン酸
テトラゾリド（ＴＰＳ−Ｔｅ）、トリイソプロピルベン
ゼンスルホン酸ニトロイミダゾリド（ＴＰＳ−ＮＩ）、
及びトリイソプロピルベンゼンスルホン酸ピリジルテト
ラゾリドなどをあげる事が出来るが、好適にはＭＳＮＴ
やＴＰＳ−Ｔｅ及びＴＰＳ−ＮＩが用いられる。反応温
度は−１０〜１００℃まで特に限定はないが通常は室温
で実施する。反応時間は使用する溶媒、反応温度によっ
て異なるが、反応溶媒としてピリジンを使用し、室温で
実施した場合は３０分である。ODN がCPG に結合してい
る場合のCPG よりの切り出し、および、次の５’末端の
置換分以外の保護基の除去は、公知の方法(J.Am.Chem.S
oc.,103,3185,(1981))によって行なうことができる。こ
のようにして得られる、一般式（１）の化合物を含む反
応混合物を、逆相およびイオン交換クロマトグラフィー
（高速液体クロマトグラフィーを含む。）等の各種クロ
マトグラフィーなど、通常の核酸の精製に用いられる精
製操作で精製することにより、前記一般式（１）を有す
る化合物を得ることができる。As the condensing agent used for the condensation, dicyclocarbodiimide (DCC), mesitylenesulfonic acid chloride (Ms-Cl), triisopropylbenzenesulfonic acid chloride, mesitylenesulfonic acid triazolide (M
ST), mesitylenesulfonic acid-3-nitrotriazolide (MSNT), triisopropylbenzenesulfonic acid tetrazolide (TPS-Te), triisopropylbenzenesulfonic acid nitroimidazolide (TPS-NI),
And triisopropylbenzene sulfonic acid pyridyl tetrazolide, etc., but preferably MSNT
And TPS-Te and TPS-NI are used. Although the reaction temperature is not particularly limited to -10 to 100 ° C, it is usually carried out at room temperature. The reaction time varies depending on the solvent used and the reaction temperature, but it is 30 minutes when the reaction is carried out at room temperature using pyridine. Cleavage from CPG when ODN is bound to CPG, and removal of the protecting groups other than the following 5'-terminal substituent are known methods (J. Am. Chem. S.
oc., 103, 3185, (1981)). The reaction mixture containing the compound of the general formula (1) thus obtained is used for usual nucleic acid purification such as reverse phase and various chromatography such as ion exchange chromatography (including high performance liquid chromatography). The compound having the above-mentioned general formula (1) can be obtained by purification by the purification procedure.
【０１７１】（第４０工程）本工程は不活性溶剤中で化
合物（２）に例えばあらかじめ文献(B.C.Freohler,P.G.
Ng and MD.Matteucci,Nucleic Acids Res.,14 5399(198
6)) に従って三塩化リンと１，２，４−トリアゾールか
ら調製したトリス−（１，２，４−トリアゾリル）ホス
ファイトを反応させた後、水を加えて反応を止め、後処
理をする事によって、ヌクレオシド３´Ｈ−ホスホネー
ト（１０）を得る工程である。用いられる溶媒としては
反応を阻害しないものであれば特に限定はないが好適に
は塩化メチレンのようなハロゲン化炭化水素である。反
応温度は−２０°〜１００℃まで特に限定はないが通常
は室温で実施する。反応時間は用いる溶媒、反応時間に
よって異なるが塩化メチレン中で室温で反応させた場合
は３０分である。(40th step) In this step, compound (2) was prepared in the presence of an inert solvent, for example, as described in the literature (BCFreohler, PG).
Ng and MD. Matteucci, Nucleic Acids Res., 14 5399 (198
6)) and reacting tris- (1,2,4-triazolyl) phosphite prepared from 1,2,4-triazole with phosphorus trichloride, and then adding water to stop the reaction and perform post-treatment. Is a step of obtaining a nucleoside 3′H-phosphonate (10). The solvent used is not particularly limited as long as it does not inhibit the reaction, but a halogenated hydrocarbon such as methylene chloride is preferable. The reaction temperature is not particularly limited from -20 ° to 100 ° C, but is usually room temperature. The reaction time varies depending on the solvent used and the reaction time, but is 30 minutes when the reaction is carried out at room temperature in methylene chloride.
【０１７２】（第４１工程）本工程は４０工程で得られ
たヌクレオシド３′Ｈ−ホスホネート（１０）とＤＮＡ
合成機で合成したＯＤＮ（３）、（４ａ）、（４ｂ）、
（５）、（６ａ）、（６ｂ）、（６ｃ）、（６ｄ）、
（７ａ）及び（７ｂ）の５′末端のジメトキシトリチル
基のみを除去し、塩基部が保護基で保護されたＣＰＧに
結合したままのＯＤＮを例えばピバロイルクロリドのよ
うな縮合剤と脱酸剤の存在下に縮合させてＨ−ホスホン
酸ジエステル結合を形成させた後に酸化剤を用いてＨ−
ホスホン酸結合をリン酸ジエステル結合に変換し、ある
いは、メトキシアミンを四塩化炭素中で反応させること
によりメトキシアミノホスフェート基に変換し塩基性条
件下でＣＰＧからＯＤＮを切り離すと同時に塩基部分の
保護基を除去して、精製操作を経て最終産物（１）を得
る工程である。本工程に用いられる溶媒としては反応を
阻害しないものであれば特に限定はないが、好適には無
水のアセトニトリルが使用される。縮合剤として用いら
れる試薬としては、カルボン酸やリン酸の酸塩化物が用
いられるが好適にはピバロイルクロリドが用いられる。(Step 41) In this step, the nucleoside 3'H-phosphonate (10) obtained in step 40 and DNA were
ODN (3), (4a), (4b), synthesized by a synthesizer,
(5), (6a), (6b), (6c), (6d),
Only the 5'-terminal dimethoxytrityl group of (7a) and (7b) is removed, and the ODN remaining bound to the CPG whose base moiety is protected by a protecting group is deoxidized with a condensing agent such as pivaloyl chloride. H-phosphonate diester bond is formed by condensation in the presence of an agent and then H-phosphonate is used with an oxidizing agent.
A phosphonic acid bond is converted into a phosphodiester bond, or a methoxyamine is converted into a methoxyaminophosphate group by reacting with methoxyamine in carbon tetrachloride to separate ODN from CPG under basic conditions and at the same time a protecting group for the base moiety. Is a step of obtaining the final product (1) through a purification operation. The solvent used in this step is not particularly limited as long as it does not inhibit the reaction, but anhydrous acetonitrile is preferably used. As the reagent used as the condensing agent, an acid chloride of carboxylic acid or phosphoric acid is used, but pivaloyl chloride is preferably used.
【０１７３】Ｈ−ホスホン酸結合を有するＯＤＮをリン
酸ジエステル型のＯＤＮに酸化する酸化剤としては、通
常、酸化反応に使用されるものであれば特に限定はな
く、過マンガン酸カリウム、二酸化マンガンのような酸
化マンガン類；四酸化ルテニウムのような酸化ルテニウ
ム類；二酸化ゼレンのようなゼレン化合物；塩化鉄のよ
うな鉄化合物；四酸化オスミウムのようなオスミウム化
合物；酸化銀のような銀化合物；酢酸水銀のような水銀
化合物、酸化鉛、四酸化鉛のような酸化鉛化合物；クロ
ム酸カリウム、クロム酸−硫酸錯体、クロム酸−ピリジ
ン錯体のようなクロム酸化合物、セリウムアンモニウム
ナイトレイト（ＣＡＮ）のようなセリウム化合物等の無
機金属酸化剤；塩素分子、臭素分子、沃素分子のような
ハロゲン分子；過沃素酸ナトリウムのような過沃素酸
類；オゾン；過酸化水素水；亜硝酸のような亜硝酸化合
物；亜塩素酸カリウム、亜塩素酸ナトリウムのような亜
塩素酸化合物；過硫酸カリウム、過硫酸ナトリウムのよ
うな過硫酸化合物等の無機酸化剤；ＤＭＳＯ酸化に使用
される試薬類（ジメチルスルホキシドとジシクロヘキシ
ルカルボジイミド、オキザリルクロリド、無水酢酸若し
くは五酸化燐との錯体又はピリジン−無水酢酸の錯
体）；ｔ−ブチルヒドロパーオキシドのようなパーオキ
シド類；トリフェニルメチルカチオンのような安定なカ
チオン類；Ｎ−ブロモコハク酸イミドのようなコハク酸
イミド類、次亜塩素酸ｔ−ブチルのような次亜塩素酸化
合物；アゾジカルボン酸メチルのようなアゾジカルボン
酸化合物；ジメチルジスルフィド、ジフェニルジスルフ
ィド、ジピリジルジスルフィドのようなジスルフィド類
とトリフェニルホスフィン；亜硝酸メチルのような亜硝
酸エステル類；四臭化メタンのようなテトラハロゲン化
炭素、２，３−ジクロロ−５，６−ジシアノ−ｐ−ベン
ゾキノン（ＤＤＱ）のようなキノン化合物等の有機酸化
剤を挙げることができ、好適にはよう素分子である。The oxidizing agent for oxidizing an ODN having an H-phosphonic acid bond to a phosphoric acid diester type ODN is not particularly limited as long as it is usually used for an oxidation reaction, and potassium permanganate, manganese dioxide and the like can be used. Oxides such as manganese oxides; ruthenium oxides such as ruthenium tetraoxide; zelenium compounds such as selene dioxide; iron compounds such as iron chloride; osmium compounds such as osmium tetroxide; silver compounds such as silver oxide; Mercury compounds such as mercury acetate, lead oxides, lead oxide compounds such as lead tetroxide; potassium chromate, chromic acid compounds such as chromic acid-sulfuric acid complex, chromic acid-pyridine complex, cerium ammonium nitrate (CAN) Inorganic metal oxidizers such as cerium compounds; Halogen molecules such as chlorine, bromine and iodine; Periodic Periodic acids such as sodium acid; ozone; hydrogen peroxide; nitrite compounds such as nitrous acid; chlorite compounds such as potassium chlorite and sodium chlorite; potassium persulfate and sodium persulfate Inorganic oxidizing agents such as persulfate compounds; reagents used for DMSO oxidation (complex of dimethyl sulfoxide and dicyclohexylcarbodiimide, oxalyl chloride, acetic anhydride or phosphorus pentoxide or pyridine-acetic anhydride complex); t- Peroxides such as butyl hydroperoxide; stable cations such as triphenylmethyl cation; succinimides such as N-bromosuccinimide, hypochlorite compounds such as t-butyl hypochlorite Azodicarboxylic acid compounds such as methyl azodicarboxylate; dimethyl disulfide, dipheni Disulfides, disulfides such as dipyridyl disulfide and triphenylphosphine; nitrites such as methyl nitrite; tetrahalogenated carbons such as methane tetrabromide, 2,3-dichloro-5,6-dicyano-p An organic oxidizing agent such as a quinone compound such as benzoquinone (DDQ) can be mentioned, and an iodine molecule is preferable.
【０１７４】使用される脱酸剤としては、ピリジン、ジ
メチルアミノピリジンのような複素環アミン類、トリメ
チルアミン、トリエチルアミン、ジイソプロピルエチル
アミンのような脂肪族アミン類があげられるが好適には
脂肪族アミン類（特にジイソプロピルエチルアミン）で
ある。 反応温度は、特に限定はないが、通常−５０乃
至５０℃であり、好適には室温である。メトキシエチル
アミノホスフェート基を形成させる反応においての溶媒
としては反応を阻害しなければ特に限定はないが、通常
は試薬である四塩化炭素を溶媒量で用いる。Examples of the deoxidizing agent used include heterocyclic amines such as pyridine and dimethylaminopyridine, and aliphatic amines such as trimethylamine, triethylamine and diisopropylethylamine, but preferably aliphatic amines ( In particular, diisopropylethylamine). The reaction temperature is not particularly limited, but is usually −50 to 50 ° C., and preferably room temperature. The solvent in the reaction for forming the methoxyethylaminophosphate group is not particularly limited as long as it does not inhibit the reaction, but carbon tetrachloride, which is a reagent, is usually used in a solvent amount.
【０１７５】反応温度は−５０℃から１００℃まで特に
限定はないが、室温で反応させる場合は反応時間は１〜
１０時間である。The reaction temperature is not particularly limited from -50 ° C to 100 ° C, but when the reaction is carried out at room temperature, the reaction time is from 1 to 1.
10 hours.
【０１７６】反応時間は、使用する原料、試薬、温度等
により異なるが、通常、５分から３０時間であり、好適
には、室温で反応した場合、３０分である。The reaction time varies depending on the starting materials used, reagents, temperature and the like, but is usually 5 minutes to 30 hours, and preferably 30 minutes when reacted at room temperature.
【０１７７】ODN がCPG に結合している場合のCPG より
の切り出し、および、次の５’末端の置換分以外の保護
基の除去は、公知の方法(J.Am.Chem.Soc.,103,3185,(19
81))によって行なうことができる。このようにして得ら
れる、一般式（１）の化合物を含む反応混合物を、逆相
およびイオン交換クロマトグラフィー（高速液体クロマ
トグラフィーを含む。）等の各種クロマトグラフィーな
ど、通常の核酸の精製に用いられる精製操作で精製する
ことにより、前記一般式（１）を有する化合物を得るこ
とができる。Cleavage from CPG when ODN is bound to CPG and removal of a protecting group other than the following 5'-terminal substituent are known methods (J. Am. Chem. Soc., 103). , 3185, (19
81)). The reaction mixture containing the compound of the general formula (1) thus obtained is used for usual nucleic acid purification such as reverse phase and various chromatography such as ion exchange chromatography (including high performance liquid chromatography). The compound having the above-mentioned general formula (1) can be obtained by purification by the purification procedure.
【０１７８】[0178]
【発明の効果】本発明の化合物はエイズウイルス（ＨＩ
Ｖー１）に対して、特異的な障害活性を有し、感染細胞
における本ウイルスの増殖を特異的に抑制しうる。した
がって、本発明の化合物はエイズ疾患の治療および予防
薬として有用である。INDUSTRIAL APPLICABILITY The compounds of the present invention are AIDS virus
It has a specific damaging activity against V-1) and can specifically suppress the growth of the virus in infected cells. Therefore, the compound of the present invention is useful as a therapeutic and prophylactic agent for AIDS disease.
【０１７９】以下に、試験例をあげて、本発明による効
果を具体的に説明する。Hereinafter, the effects of the present invention will be specifically described with reference to test examples.
【０１８０】[0180]
【試験例１】修飾オリゴデオキシリボヌクレオチドの抗
HIV-1 活性の測定 抗HIV-1 活性はパウエルらの方法によって測定した（R.
Pauel et al., J. Virological Methods 20, 309-321(1
988)) 。すなわち, 対数増殖期にあるＭＴ−４細胞を15
0 × gで5 分間遠心し，得られた細胞沈澱を培地にて懸
濁したのちHIV-1 (IIIB 型) を10 CCID50 の濃度で37℃
で1 時間感染させた。その後, 牛胎児血清10% を含むRP
MI-1640 培地( 以下「血清培地」と称する) で遠心し、
洗浄することによりHIV-1 感染ＭＴー４細胞を得た。[Test Example 1] Antibodies of modified oligodeoxyribonucleotides
Measurement of HIV-1 activity Anti-HIV-1 activity was measured by the method of Powell et al.
Pauel et al., J. Virological Methods 20, 309-321 (1
988)). That is, 15 MT-4 cells in the logarithmic growth phase were
Centrifuge at 0 × g for 5 minutes, suspend the resulting cell pellet in the medium, and collect HIV-1 (IIIB type) at a concentration of 10 CCID 50 at 37 ° C.
Infected for 1 hour. Then, RP containing 10% fetal bovine serum
Centrifuge in MI-1640 medium (hereinafter referred to as "serum medium"),
By washing, HIV-1 infected MT-4 cells were obtained.
【０１８１】HIV-1 感染MT-4細胞およびHIV-1 非感染MT
-4細胞をそれぞれ4 ×105 細胞/ mlになるように血清培
地に懸濁した。96穴プラスチックマイクロタイタープレ
ート中にあらかじめ段階希釈した検体化合物溶液( 血清
培地に溶解したもの) を各穴に100 μl づつ入れ, 次い
でこの各穴に上記細胞懸濁液を各々100 μl づつ添加
し, 5%の炭酸ガス存在下で6 日間静置培養した。HIV-1 infected MT-4 cells and HIV-1 uninfected MT
-4 cells were suspended in serum medium at 4 × 10 5 cells / ml. 100 μl of the serially diluted sample compound solution (dissolved in serum medium) was put into each well in a 96-well plastic microtiter plate, and then 100 μl of the above cell suspension was added to each well. Static culture was carried out for 6 days in the presence of 5% carbon dioxide.
【０１８２】同様に, 検体化合物添加のHIV-1 感染MT-4
細胞および検体化合物無添加のHIV-1 非感染MT-4細胞を
培養した。Similarly, HIV-1 infected MT-4 supplemented with a test compound was added.
Cells and HIV-1 non-infected MT-4 cells without addition of the test compound were cultured.
【０１８３】培養終了後，MTT(3-(4,5-dimethylthiazol
e-2-yl)-2,5-diphenyltetrazoliumbromide)法に基づき,
生細胞数を測定し(L.M.Green et al., J. Immunol. Me
thods, 70, 257-268(1984)), HIV-1 による細胞障害活
性を求めた。検体化合物無添加のHIV-1 感染MT-4細胞の
細胞障害活性を100%とし、検体化合物無添加のHIV-1(II
IB 型) 非感染ＭＴー４細胞の細胞障害活性を０％とし
て、HIV-1 感染ＭＴー４細胞の細胞障害活性を５０％抑
制しうる検体の濃度（ＩＣ50) を求めた。また、検体化
合物の細胞毒性活性として、HIV-1 非感染ＭＴー４細胞
の増殖を５０％抑制する濃度（ＣＣ50）を求めた。これ
らの測定結果を表２に示す。After completion of the culture, MTT (3- (4,5-dimethylthiazol
e-2-yl) -2,5-diphenyltetrazoliumbromide) method,
The number of viable cells was measured (LM Green et al., J. Immunol. Me.
thods, 70, 257-268 (1984)), and the cytotoxic activity by HIV-1 was sought. The cytotoxic activity of HIV-1 infected MT-4 cells without added sample compound was set to 100%, and HIV-1 (II
IB type) The cytotoxic activity of non-infected MT-4 cells was defined as 0%, and the concentration of the sample (IC 50 ) that could suppress the cytotoxic activity of HIV-1 infected MT-4 cells by 50% was determined. As the cytotoxic activity of the test compound, a concentration (CC 50 ) at which the proliferation of HIV-1 non-infected MT-4 cells was suppressed by 50% was determined. The results of these measurements are shown in Table 2.
【０１８４】[0184]
【表２】 その結果、表２にあげた修飾オリゴデオキシリボヌクレ
オチドはいずれも，特に高い抗HIV-1 活性を有すること
が明かとなった。[Table 2] As a result, it was revealed that each of the modified oligodeoxyribonucleotides listed in Table 2 has a particularly high anti-HIV-1 activity.
【０１８５】これらの化合物はいずれも１０μｇ／ｍｌ
以下の濃度で抗HIV-1 活性を示した。All of these compounds were 10 μg / ml
It exhibited anti-HIV-1 activity at the following concentrations.
【０１８６】以下に示す化学式中の塩基配列（例えば、
TGGGAeG ）は、特に断りがない場合は、それぞれ５′末
端より対応する塩基配列をもつオリゴデオキシリボヌク
レオチドのトリエチルアミン塩を表わし、５′末端と
３′末端の水酸基を含まないものとする。The nucleotide sequences in the chemical formulas shown below (for example,
Unless otherwise specified, TGGGAeG) represents a triethylamine salt of an oligodeoxyribonucleotide having a corresponding base sequence from the 5'end, and does not include hydroxyl groups at the 5'end and 3'end.
【０１８７】なお、目的化合物を示すのに、適宜、化学
名又は構造式を用いた。Chemical names or structural formulas were used as appropriate to indicate the target compound.
【０１８８】[0188]
【実施例１】 （１ａ）５′−０−［(3,4- ジベンジルオキシ）ベンジ
ル］チミジン ３′−０−［（1,1-ジメチルエチル）ジメチルシリル］
チミジン(Can.J.Chem.,56,2768(1978)) ７１３mg（２mm
ol）を４mLのテトラヒドロフランに溶解し、アルゴン雰
囲気下で、１７５mg（４mmol）の５５％NaH を加えて、
６０℃で２時間撹拌した。室温に戻した後、3,4-（ジベ
ンジルオキシ）ベンジルブロミド（Chem.Ber.,102,288
7,(1969) ）６７８mg（２mmol）のテトラヒドロフラン
１mL溶液を滴下し、次いで、ヨウ化ナトリウム149.9mg
（１mmol）を加えて、室温で撹拌した。１６時間後、減
圧下溶媒を留去し、残渣を５０mLの酢酸エチルに溶解
し、酢酸エチル溶液を５０mLの0.01N HCl 水溶液で２回
洗浄し、無水硫酸マグネシウムで乾燥した。溶媒を減圧
下留去し、残渣を１００ｇ（２３０−４００mesh）のシ
リカゲルカラムにアプライして、0.5 〜３％メタノール
／塩化メチレンで溶出することにより、３′−０−
［（1,1-ジメチルエチル）ジメチルシリル］−５′−０
−［(3,4- ジベンジルオキシ）ベンジル］チミジンを含
む混合物を得た。これを1.93mLのテトラヒドロフランに
溶解し、テトラブチルアンモニウムフロリドのテトラヒ
ドロフラン溶液（１Ｍ）を1.93mL加えて、室温で撹拌し
た。３０分後、減圧下溶媒を留去し、残渣を５０mLの酢
酸エチルに溶解し、酢酸エチル溶液を５０mLの飽和食塩
水で２回洗浄し、無水硫酸マグネシウムで乾燥した。減
圧下に溶媒を留去して、残渣を３０ｇ（２３０−４００
mesh）のシリカゲルカラムにアプライし、１〜３％メタ
ノール／塩化メチレンで溶出することにより、345.4mg
(31.7％) の目的化合物を得た。Example 1 (1a) 5′-0-[(3,4-dibenzyloxy) benzyl
Lu] thymidine 3′-0-[(1,1-dimethylethyl) dimethylsilyl]
Thymidine (Can.J.Chem., 56,2768 (1978)) 713mg (2mm
ol) was dissolved in 4 mL of tetrahydrofuran, and 175 mg (4 mmol) of 55% NaH was added under an argon atmosphere,
The mixture was stirred at 60 ° C for 2 hours. After returning to room temperature, 3,4- (dibenzyloxy) benzyl bromide (Chem.Ber., 102,288
7 (1969)) 678 mg (2 mmol) in 1 mL of tetrahydrofuran was added dropwise, and then sodium iodide 149.9 mg
(1 mmol) was added, and the mixture was stirred at room temperature. After 16 hours, the solvent was evaporated under reduced pressure, the residue was dissolved in 50 mL of ethyl acetate, the ethyl acetate solution was washed twice with 50 mL of 0.01N HCl aqueous solution, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, the residue was applied to a silica gel column of 100 g (230-400 mesh) and eluted with 0.5-3% methanol / methylene chloride to give 3'-0-.
[(1,1-Dimethylethyl) dimethylsilyl] -5'-0
A mixture containing-[(3,4-dibenzyloxy) benzyl] thymidine was obtained. This was dissolved in 1.93 mL of tetrahydrofuran, 1.93 mL of a tetrahydrofuran solution (1M) of tetrabutylammonium fluoride was added, and the mixture was stirred at room temperature. After 30 minutes, the solvent was evaporated under reduced pressure, the residue was dissolved in 50 mL of ethyl acetate, the ethyl acetate solution was washed twice with 50 mL of saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and 30 g of the residue (230-400
mesh) silica gel column and eluted with 1-3% methanol / methylene chloride to give 345.4mg
(31.7%) of the target compound was obtained.
【０１８９】1H-NMR(270MHz,CDCl3,TMS)δppm:8.26(1H,
s,NH),7.50(1H,s,H6),7.47-7.28(10H、m),6.91-6.79(3H,
m),6.36(1H,t,H1',J=6.75Hz),5.17(4H,s,PhCH2 ),4.47,
4.45(2H,2s,PhCH2 OCH2),4.41-4.36(1H,m,H3'),4.04-4.0
1(1H,m,H4'),3.72-3.56(2H,m,H5'),2.31-2.05(2H,m,H
2'),1.62(3H,s,CH3). （１ｂ）５′−０−［(3,4- ジベンジルオキシ）ベンジ
ル］チミジン−３′−０−（２−シアノエチル Ｎ，Ｎ
−ジイソプロピル）ホスホロアミダイト 実施例１ａの化合物271.7mg(0.499mmol)をピリジンで３
回共沸して乾燥した後、１０mLのテトラヒドロフランに
溶解し、1.39mL（８mmol）のジイソプロピルエチルアミ
ンと0.822mL(４mmol）の２−シアノエチル Ｎ，Ｎ−ジ
イソプロピルクロロホスホロアミダイトを加え、アルゴ
ン雰囲気下、室温で撹拌した。３０分後に沈殿をろ過し
て除き、溶媒を減圧下留去した。残渣を１００mLの酢酸
エチルに溶解し、酢酸エチル溶液を氷冷した５０mLの１
０％Na2CO3水で２回洗浄して、無水硫酸ナトリウムで乾
燥した。溶媒を減圧下留去した後、残渣を４０ｇ(70-23
0mesh)のシリカゲルを含むカラムにアプライし、塩化メ
チレン：酢酸エチル：トリエチルアミン(45:45:10,v/v/
v)で溶出することにより、286.9mg （７７％）の目的化
合物を得た。 1 H-NMR (270 MHz, CDCl 3 , TMS) δppm: 8.26 (1 H,
s, NH), 7.50 (1H, s, H6), 7.47-7.28 (10H, m), 6.91-6.79 (3H,
m), 6.36 (1H, t, H1 ', J = 6.75Hz), 5.17 (4H, s, PhC H 2 ), 4.47,
4.45 (2H, 2s, PhC H 2 OCH 2 ), 4.41-4.36 (1H, m, H3 '), 4.04-4.0
1 (1H, m, H4 '), 3.72-3.56 (2H, m, H5'), 2.31-2.05 (2H, m, H
2 '), 1.62 (3H, s, CH 3) (1b) 5'-0 -. [(3,4- di benzyloxy) benzylidene
Lu] thymidine-3′-0- (2-cyanoethyl N, N
-Diisopropyl) phosphoramidite 271.7 mg (0.499 mmol) of the compound of Example 1a was treated with pyridine 3 times.
After being azeotropically dried and dissolved in 10 mL of tetrahydrofuran, 1.39 mL (8 mmol) of diisopropylethylamine and 0.822 mL (4 mmol) of 2-cyanoethyl N, N-diisopropylchlorophosphoramidite were added, and under an argon atmosphere, Stir at room temperature. After 30 minutes, the precipitate was filtered off and the solvent was evaporated under reduced pressure. The residue was dissolved in 100 mL of ethyl acetate and the ethyl acetate solution was ice-cooled in 50 mL of 1 mL.
It was washed twice with 0% Na 2 CO 3 water and dried over anhydrous sodium sulfate. After distilling off the solvent under reduced pressure, 40 g (70-23
(0 mesh) silica gel column, methylene chloride: ethyl acetate: triethylamine (45:45:10, v / v /
Elution with v) gave 286.9 mg (77%) of the desired compound.
【０１９０】1H-NMR(270MHz,CDCl3,TMS)δppm:8.07(1H,
bs,NH),7.53,7.51(1H,2s,H6),7.45-7.25,6.92-6.81(13
H,m,Ph),6.37(1H,t,H1',J=6.60Hz),5.15(4H,s,PhCH2 ),
4.62-4.53(1H,m,H3'),4.47(2H,s,PhCH2 OCH2),4.22,4.14
(1H,2bs,H4'),3.90-3.53(6H,m,H5',POCH2 ,PNCH),2.68-
2.53(2H,m,NCCH2 ),2.47-2.05(2H,m,H2'),1.58(3H,s,C
H3),1.17(12H,d,(CH3 )2CH,J=5.94Hz). （１ｃ） 1 H-NMR (270 MHz, CDCl 3 , TMS) δ ppm: 8.07 (1 H,
bs, NH), 7.53,7.51 (1H, 2s, H6), 7.45-7.25,6.92-6.81 (13
H, m, Ph), 6.37 (1H, t, H1 ', J = 6.60Hz), 5.15 (4H, s, PhC H 2 ),
4.62-4.53 (1H, m, H3 '), 4.47 (2H, s, PhC H 2 OCH 2 ), 4.22,4.14
(1H, 2bs, H4 '), 3.90-3.53 (6H, m, H5', POC H 2 , PNC H ), 2.68-
2.53 (2H, m, NCC H 2 ), 2.47-2.05 (2H, m, H2 '), 1.58 (3H, s, C
H 3 ), 1.17 (12H, d, (C H 3 ) 2 CH, J = 5.94Hz). (1c)
【０１９１】[0191]
【化１８】 [Chemical 18]
【０１９２】ミリジェン／バイオサーチ（日本ミリポア
・リミテッド社製）のCycloneTM Plus DNA/RNA シンセ
サイザーに、付属する合成用試薬類と、合成用のプログ
ラムとして15.0μmoleアミダイトカ−トリッジを接続し
た。但し、このとき、チミジンに対応するβ−シアノエ
チルアミダイト溶液のかわりに、３５mMに調製した実施
例１ｂの化合物のアセトニトリル溶液を用い、固相担体
としては、５００Åコントロールドポアグラス（CPG ）
充てん剤で、３４μmol/g のG-CPG を１４７mg（５μmo
l ）はかりとり、15.0μmol 用エンプティーカラムにつ
めて使用した。ＴＧＧＧＡＧという塩基配列を入力し、
最後のＴを結合させた後には酸処理を行わない設定のプ
ログラムを作動させた。但し、１回目のカップリングで
Ａ−ベータアミダイトを反応させた後は、酸化溶液（ヨ
ウ素溶液）で酸化せずに、シンセサイザーからカラムを
取り外し、５ｍｌのテトラエチルチウラム ジスルフィ
ド（TETD）／アセトニトリル溶液（アプライド バイオ
システムズ）をカラムに入れ、室温で１５分間放置し
た。アセトニトリルで洗浄し、再びシンセサイザーに取
り付けた。この操作により、ＣＰＧ上に保護されたオリ
ゴヌクレオチドが構築された誘導体を得た。これを減圧
下乾燥したのちにカラムからとり出し、約１０ｍｌの２
９％アンモニア水に浸して密閉し、室温で約２日間反応
した。CPG をろ過により除き、１０ｍｌの水で２回洗浄
した。ろ液と洗浄液を合わせて、１０ｍｌまで濃縮し、
１０mLの酢酸エチルで３回洗浄し、水溶液を約３ｍｌに
濃縮した。これを逆相カラムクロマトグラフィー（Prep
arative C18, Waters, 1.5 x 15 cm, 50 mM 炭酸水素ト
リエチルアミン水溶液 (TEAB) 及びアセトニトリル, 2
0-50%CH3CN/TEAB-linear gradient, 254 nm ）で精製
し、アモルファス状の目的物１ｃを175 OD(260nm) 得
た。これを逆相HPLC（Inertsil ODS-2, 6 x 150mm, A:
0.1 M 酢酸トリエチルアミン水溶液（TEAA, pH 7.0）,
B:アセトニトリル, B/(A+B)=0.28, 1ml/min, 60 ℃, 2
60 nm）で分析すると12.26minに溶出された。A Cyclone ™ Plus DNA / RNA synthesizer manufactured by Milligen / Biosearch (manufactured by Japan Millipore Limited) was connected with the attached reagents for synthesis and a 15.0 μmole amidite cartridge as a program for synthesis. However, at this time, instead of the β-cyanoethylamidite solution corresponding to thymidine, an acetonitrile solution of the compound of Example 1b adjusted to 35 mM was used, and the solid phase carrier was 500 Å controlled pore glass (CPG).
As a packing material, 147 mg (5 μmo) of 34 μmol / g G-CPG was used.
l) Weighed and used by filling an empty column for 15.0 μmol. Enter the base sequence TGGGAG,
After coupling the last T, the program was run with no acid treatment. However, after reacting the A-beta amidite with the first coupling, the column was removed from the synthesizer without being oxidized with an oxidizing solution (iodine solution), and 5 ml of tetraethylthiuram disulfide (TETD) / acetonitrile solution (Applied Biosystems) was placed in the column and left at room temperature for 15 minutes. It was washed with acetonitrile and reattached to the synthesizer. By this operation, a derivative in which a protected oligonucleotide was constructed on CPG was obtained. After drying it under reduced pressure, it was taken out from the column, and about 10 ml of 2
It was soaked in 9% ammonia water and hermetically sealed, and reacted at room temperature for about 2 days. CPG was removed by filtration and washed twice with 10 ml of water. The filtrate and washing solution are combined and concentrated to 10 ml,
It was washed 3 times with 10 mL of ethyl acetate and the aqueous solution was concentrated to about 3 ml. Reverse phase chromatography (Prep
arative C18, Waters, 1.5 x 15 cm, 50 mM triethylamine bicarbonate aqueous solution (TEAB) and acetonitrile, 2
It was purified by 0-50% CH 3 CN / TEAB-linear gradient, 254 nm) to obtain 175 OD (260 nm) of amorphous target product 1c. Reverse phase HPLC (Inertsil ODS-2, 6 x 150mm, A:
0.1 M triethylamine acetate aqueous solution (TEAA, pH 7.0),
B: Acetonitrile, B / (A + B) = 0.28, 1ml / min, 60 ℃, 2
It was eluted at 12.26 min when analyzed at 60 nm).
【０１９３】UVmax(H2O)：255 nmUVmax (H 2 O): 255 nm
【０１９４】[0194]
【実施例２】Example 2
【０１９５】[0195]
【化１９】 [Chemical 19]
【０１９６】以下の操作を除き、実施例１ｃと同様にし
て実施例２の化合物を合成した。すなわち、２回目のカ
ップリングでＧ−ベータアミダイトを反応させた後は、
酸化溶液（ヨウ素溶液）で酸化せずに、シンセサイザー
からカラムを取り外し、５ｍｌのTETD／アセトニトリル
溶液をカラムに入れ、室温で１５分間放置した。アセト
ニトリルで洗浄し、再びシンセサイザーに取り付けた。
また、精製においては、逆相カラムクロマトグラフィー
（Preparative C18, Waters, 1.5 x 15 cm, 50mM TEAB
及びアセトニトリル, 20-50%CH3CN-TEAB linear gradie
nt, 254 nm）を行い、アモルファス状の化合物を181 OD
(260nm) 得た。本化合物を逆相HPLC（Inertsil ODS-2,
6 x 150mm, A:0.1 M TEAA （pH 7.0）, B:アセトニトリ
ル, B/(A+B)=0.28, 1ml/min, 60 ℃, 260 nm）で分析す
ると12.46minに溶出された。The compound of Example 2 was synthesized in the same manner as in Example 1c except for the following operations. That is, after reacting the G-beta amidite with the second coupling,
The column was removed from the synthesizer without being oxidized with an oxidizing solution (iodine solution), 5 ml of TETD / acetonitrile solution was put into the column, and left at room temperature for 15 minutes. It was washed with acetonitrile and reattached to the synthesizer.
For purification, reverse-phase column chromatography (Preparative C18, Waters, 1.5 x 15 cm, 50 mM TEAB
And acetonitrile, 20-50% CH 3 CN-TEAB linear gradie
nt, 254 nm) to remove the amorphous compound at 181 OD.
(260 nm) was obtained. This compound was analyzed by reverse phase HPLC (Inertsil ODS-2,
Analysis at 6 x 150 mm, A: 0.1 M TEAA (pH 7.0), B: acetonitrile, B / (A + B) = 0.28, 1 ml / min, 60 ° C, 260 nm) revealed eluting at 12.46 min.
【０１９７】UVmax(H2O)：２５４ ｎｍUVmax (H 2 O): 254 nm
【０１９８】[0198]
【実施例３】Example 3
【０１９９】[0199]
【化２０】 Embedded image
【０２００】以下の操作を除き、実施例１ｃと同様にし
て実施例３の化合物を合成した。すなわち、２回目と３
回目のカップリングでＧ−ベータアミダイトを反応させ
た後は、酸化溶液（ヨウ素溶液）で酸化せずに、シンセ
サイザーからカラムを取り外し、５ｍｌのＴＥＴＤ／ア
セトニトリル溶液をカラムに入れ、室温で１５分間放置
した。アセトニトリルで洗浄し、再びシンセサイザーに
取り付けた。また、精製においては、逆相カラムクロマ
トグラフィー（Preparative C18, Waters, 1.5 x15 c
m, 50 mM TEAB及びアセトニトリル, 20-50%CH3CN-TEAB
linear gradient,254 nm）を行い、アモルファス状の
化合物を143 OD(260nm) 得た。本化合物を逆相HPLC（In
ertsil ODS-2, 6 x 150mm, A:0.1 M TEAA （pH 7.0）,
B:アセトニトリル, B/(A+B)=0.28, 1ml/min, 60 ℃, 26
0 nm）で分析すると12.40minに溶出された。The compound of Example 3 was synthesized in the same manner as in Example 1c except for the following operations. That is, the second time and 3
After reacting the G-beta amidite with the second coupling, remove the column from the synthesizer without oxidizing it with an oxidizing solution (iodine solution), put 5 ml of TETD / acetonitrile solution into the column, and leave at room temperature for 15 minutes. did. It was washed with acetonitrile and reattached to the synthesizer. For purification, reverse-phase column chromatography (Preparative C18, Waters, 1.5 x15 c
m, 50 mM TEAB and acetonitrile, 20-50% CH 3 CN-TEAB
Linear gradient, 254 nm) was performed to obtain 143 OD (260 nm) of an amorphous compound. This compound was analyzed by reverse phase HPLC (In
ertsil ODS-2, 6 x 150mm, A: 0.1 M TEAA (pH 7.0),
B: Acetonitrile, B / (A + B) = 0.28, 1ml / min, 60 ℃, 26
It was eluted at 12.40 min when analyzed at 0 nm).
【０２０１】UVmax(H2O)：254 nmUVmax (H 2 O): 254 nm
【０２０２】[0202]
【実施例４】Embodiment 4
【０２０３】[0203]
【化２１】 [Chemical 21]
【０２０４】以下の操作を除き、実施例１ｃと同様にし
て実施例４の化合物を合成した。すなわち、２回目と３
回目と４回目のカップリングでＧ−ベータアミダイトを
反応させた後は、酸化溶液（ヨウ素溶液）で酸化せず
に、シンセサイザーからカラムを取り外し、５ｍｌのTE
TD／アセトニトリル溶液をカラムに入れ、室温で１５分
間放置した。アセトニトリルで洗浄し、再びシンセサイ
ザーに取り付けた。また、精製においては、逆相カラム
クロマトグラフィー（Preparative C18, Waters,1.5 x
15 cm,50 mM TEAB 及びアセトニトリル, 20-50%CH3CN-T
EAB linear gradient, 254 nm）を行い、アモルファス
状の化合物を174 OD(260nm) 得た。本化合物を逆相HPLC
（Inertsil ODS-2, 6 x 150mm, A:0.1 M TEAA （pH 7.
0）, B:アセトニトリル, B/(A+B)=0.28, 1ml/min,60℃,
260 nm）で分析すると12.59minに溶出された。The compound of Example 4 was synthesized in the same manner as in Example 1c except for the following operations. That is, the second time and 3
After reacting the G-beta amidite with the 4th and 4th couplings, remove the column from the synthesizer without oxidizing with the oxidizing solution (iodine solution), and remove 5 ml of TE.
The TD / acetonitrile solution was placed in the column and left at room temperature for 15 minutes. It was washed with acetonitrile and reattached to the synthesizer. For purification, reverse phase column chromatography (Preparative C18, Waters, 1.5 x
15 cm, 50 mM TEAB and acetonitrile, 20-50% CH 3 CN-T
EAB linear gradient, 254 nm) was performed to obtain 174 OD (260 nm) of an amorphous compound. Reverse phase HPLC of this compound
(Inertsil ODS-2, 6 x 150mm, A: 0.1 M TEAA (pH 7.
0), B: acetonitrile, B / (A + B) = 0.28, 1ml / min, 60 ℃,
It was eluted at 12.59 min when analyzed at 260 nm).
【０２０５】UVmax(H2O)：254 nmUVmax (H 2 O): 254 nm
【０２０６】[0206]
【実施例５】Example 5
【０２０７】[0207]
【化２２】 [Chemical formula 22]
【０２０８】以下の操作を除き、実施例１ｃと同様にし
て実施例５の化合物を合成した。２回目と３回目と４回
目のカップリングでＧ−ベータアミダイトを反応させた
後と、５回目のカップリングで実施例１ｂの化合物を反
応させた後は、酸化溶液（ヨウ素溶液）で酸化せずに、
シンセサイザーからカラムを取り外し、５ｍｌのTETD／
アセトニトリル溶液をカラムに入れ、室温で１５分間放
置した。アセトニトリルで洗浄し、再びシンセサイザー
に取り付けた。また、精製においては、逆相カラムクロ
マトグラフィー（Prevarative C18, Waters, 1.5 x 15
cm,50 mM TEAB及びアセトニトリル, 20-50%CH3CN-TEAB
linear gradient, 254 nm）を行い、アモルファス状の
化合物を161 OD(260nm) 得た。本化合物を逆相HPLC（In
ertsil ODS-2, 6 x 150mm, A:0.1 M TEAA （pH 7.0）,
B:アセトニトリル, B/(A+B)=0.28, 1ml/min, 60℃, 26
0 nm）で分析すると18.02minに溶出された。The compound of Example 5 was synthesized in the same manner as in Example 1c except for the following operations. After the G-beta amidite was reacted in the second, third, and fourth couplings, and the compound of Example 1b was reacted in the fifth coupling, it was oxidized with an oxidizing solution (iodine solution). Without
Remove the column from the synthesizer and add 5 ml TETD /
The acetonitrile solution was put into the column and left at room temperature for 15 minutes. It was washed with acetonitrile and reattached to the synthesizer. For purification, reverse-phase column chromatography (Prevarative C18, Waters, 1.5 x 15
cm, 50 mM TEAB and acetonitrile, 20-50% CH 3 CN-TEAB
Linear gradient, 254 nm) was performed to obtain 161 OD (260 nm) of an amorphous compound. This compound was analyzed by reverse phase HPLC (In
ertsil ODS-2, 6 x 150mm, A: 0.1 M TEAA (pH 7.0),
B: Acetonitrile, B / (A + B) = 0.28, 1ml / min, 60 ℃, 26
It was eluted at 18.02 min when analyzed at 0 nm).
【０２０９】UVmax(H2O)：255 nmUVmax (H 2 O): 255 nm
【０２１０】[0210]
【実施例６】Example 6
【０２１１】[0211]
【化２３】 [Chemical formula 23]
【０２１２】５００Å コントロールドポアグラス（CP
G ）充てん剤であるG-CPG （３０μｍｏｌ、８７０ｍ
ｇ）に対し、以下の操作を行った（以下のＨ−ホスホネ
ートユニットのカップリングの操作を以後「Ｈ−ホスホ
ネート カップリング」という）。G-CPG 担体をフィル
ター付きカラム管に入れ、デブロッキング溶液（２ｍ
ｌ）を加え、１分間放置した後、塩化メチレン（２ｍ
ｌ）で３回洗浄した。デブロッキングをさらに１回繰り
返した後、窒素を担体に５分間吹き付け、乾燥した。担
体にＡ−Ｈ−ホスホネート（１１５ｍｇ，１２０μｍｏ
ｌ、日本ミリポア・リミテッド）を１．５ｍｌのピリジ
ン−アセトニトリル（１：１ｖ／ｖ）溶液に溶解したも
のを加えた後、Ｈ−ホスホネート活性化剤（２４０ｍ
ｇ、１．２ｍｍｏｌ、日本ミリポア・リミテッド）を
１．５ｍｌのピリジン−アセトニトリル（１：１ｖ／
ｖ）溶液に溶解したものを加え、室温で１０分間放置し
た。担体を塩化メチレン（２ｍｌ）で２回洗浄し、窒素
を担体に５分間吹き付け乾燥した。担体にイソプロピル
ホスホネート（Tetrahedron Letters 29, 861-864(198
8), １１．２ｍｇ、１２０μｍｏｌ）を１．５ｍｌの
ピリジン−アセトニトリル（１：１ｖ／ｖ）溶液に溶解
したものを加えた後、Ｈ−ホスホネート活性化剤（２４
０ｍｇ、１．２ｍｍｏｌ、日本ミリポア・リミテッド）
を１．５ｍｌのピリジン−アセトニトリル（１：１ｖ／
ｖ）溶液に溶解したものを加え、室温で１０分間放置し
た。担体を塩化メチレン（２ｍｌ）で２回洗浄した。500Å Controlled pore glass (CP
G) G-CPG as a packing material (30 μmol, 870 m
For g), the following operation was performed (hereinafter, the operation of coupling the H-phosphonate unit is referred to as “H-phosphonate coupling”). Place the G-CPG carrier in a column tube with filter and remove the deblocking solution (2 m
l) was added and left for 1 minute, then methylene chloride (2 m
Washed 3 times with l). After deblocking was repeated once more, nitrogen was blown onto the carrier for 5 minutes and dried. AH-phosphonate (115 mg, 120 μmo on carrier)
l, Nippon Millipore Limited) dissolved in 1.5 ml of pyridine-acetonitrile (1: 1 v / v) solution was added, and then H-phosphonate activator (240 m
g, 1.2 mmol, Nippon Millipore Limited) and 1.5 ml of pyridine-acetonitrile (1: 1 v /
v) What was dissolved in the solution was added and left at room temperature for 10 minutes. The carrier was washed twice with methylene chloride (2 ml) and nitrogen was blown onto the carrier for 5 minutes to dry. Isopropylphosphonate (Tetrahedron Letters 29, 861-864 (198
8), 11.2 mg, 120 μmol) dissolved in 1.5 ml pyridine-acetonitrile (1: 1 v / v) solution was added, followed by H-phosphonate activator (24
0 mg, 1.2 mmol, Japan Millipore Limited)
1.5 ml of pyridine-acetonitrile (1: 1 v /
v) What was dissolved in the solution was added and left at room temperature for 10 minutes. The carrier was washed twice with methylene chloride (2 ml).
【０２１３】Ｈ−ホスホネート カップリングが終了し
た後、担体（１４５ｍｇ、５μｍｏｌ）に１０％メトキ
シエチルアミン／四塩化炭素溶液を２ｍｌ加え、室温で
３０分間放置後、アセトニトリルで洗浄した。After the H-phosphonate coupling was completed, 2 ml of 10% methoxyethylamine / carbon tetrachloride solution was added to the carrier (145 mg, 5 μmol), and the mixture was left at room temperature for 30 minutes and washed with acetonitrile.
【０２１４】この担体と実施例１ｃのＤＮＡ／ＲＮＡシ
ンセサイザーを用いて、実施例１ｃと同様にＤＮＡ鎖を
伸長した。但し、ＴＧＧＧＡという塩基配列を入力し、
TETD／アセトニトリル溶液を用いた硫化反応は行わず、
酸化溶液（ヨウ素溶液）による酸化反応を行った。精製
においては、逆相HPLC（Inertsil PREP-ODS, 20 x 250
mm, A:0.1 M TEAA (pH 7.0), B: アセトニトリル, 7ml/
min, B/(A+B)=0.32,260 nmを行い、17.4分に溶出する
分画を集めた。減圧下にアセトニトリルを留去したのち
に凍結乾燥し、水に溶かして再度凍結乾燥して、アモル
ファス状の化合物を102 OD(260nm) 得た。本化合物を逆
相HPLC（Inertsil ODS-2, 6 x 150mm, A:0.1 M TEAA
（pH 7.0）, B:アセトニトリル, B/(A+B)=0.32, 1ml/mi
n, 60 ℃,260 nm）で分析すると6.33min に溶出され
た。Using this carrier and the DNA / RNA synthesizer of Example 1c, the DNA chain was extended in the same manner as in Example 1c. However, enter the base sequence TGGGA,
No sulfurization reaction using TETD / acetonitrile solution
An oxidation reaction was performed with an oxidizing solution (iodine solution). For purification, reverse-phase HPLC (Inertsil PREP-ODS, 20 x 250
mm, A: 0.1 M TEAA (pH 7.0), B: Acetonitrile, 7 ml /
min, B / (A + B) = 0.32, 260 nm was performed, and fractions eluting at 17.4 minutes were collected. After distilling off acetonitrile under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to obtain 102 OD (260 nm) of an amorphous compound. Reverse phase HPLC (Inertsil ODS-2, 6 x 150mm, A: 0.1 M TEAA)
(PH 7.0), B: Acetonitrile, B / (A + B) = 0.32, 1ml / mi
n, 60 ℃, 260 nm), it was eluted at 6.33 min.
【０２１５】UVmax(H2O)：255 nmUVmax (H 2 O): 255 nm
【０２１６】[0216]
【実施例７】Example 7
【０２１７】[0219]
【化２４】 [Chemical formula 24]
【０２１８】５００Å コントロールドポアグラス（CP
G ）充てん剤であるG-CPG （３０μｍｏｌ、８７０ｍ
ｇ）に対し、Ａ−Ｈ−ホスホネート カップリングとＧ
−Ｈ−ホスホネート カップリングを順に行った。500Å Controlled pore glass (CP
G) G-CPG as a packing material (30 μmol, 870 m
g) to A-H-phosphonate coupling and G
The -H-phosphonate coupling was performed sequentially.
【０２１９】Ｈ−ホスホネート カップリングが終了し
た後、担体（１４５ｍｇ、５μｍｏｌ）に１０％メトキ
シエチルアミン／四塩化炭素溶液を２ｍｌ加え室温で３
０分間放置後、アセトニトリルで洗浄した。After the H-phosphonate coupling was completed, 2 ml of 10% methoxyethylamine / carbon tetrachloride solution was added to the carrier (145 mg, 5 μmol) and the mixture was allowed to stand at room temperature for 3 hours.
After leaving it for 0 minutes, it was washed with acetonitrile.
【０２２０】この担体と実施例１ｃのＤＮＡ／ＲＮＡシ
ンセサイザーを用いて、実施例１ｃと同様にＤＮＡ鎖を
伸長した。但し、ＴＧＧＧという塩基配列を入力し、TE
TD／アセトニトリル溶液を用いた硫化反応は行わず、酸
化溶液（ヨウ素溶液）による酸化反応を行った。精製に
おいては、逆相HPLC（Inertsil PREP-ODS, 20 x 250mm,
A:0.1 M TEAA (pH 7.0), B: アセトニトリル, 7ml/mi
n, B/(A+B)=0.32, 260 nm）を行い、20.0分に溶出する
分画を集めた。減圧下にアセトニトリルを留去した後、
凍結乾燥し、水に溶かして再度凍結乾燥して、アモルフ
ァス状の化合物を52 OD(260nm)得た。本化合物を逆相HP
LC（Inertsil ODS-2, 6 x 150mm, A:0.1M TEAA （pH 7.
0）, B:アセトニトリル, B/(A+B)=0.32, 1ml/min, 60
℃, 260nm）で分析すると6.62min に溶出された。Using this carrier and the DNA / RNA synthesizer of Example 1c, the DNA chain was extended in the same manner as in Example 1c. However, enter the base sequence TGGG,
The sulfurization reaction using the TD / acetonitrile solution was not performed, but the oxidation reaction was performed using an oxidizing solution (iodine solution). For purification, reverse-phase HPLC (Inertsil PREP-ODS, 20 x 250 mm,
A: 0.1 M TEAA (pH 7.0), B: Acetonitrile, 7ml / mi
n, B / (A + B) = 0.32, 260 nm) was performed, and fractions eluting at 20.0 minutes were collected. After distilling off acetonitrile under reduced pressure,
It was freeze-dried, dissolved in water and freeze-dried again to obtain 52 OD (260 nm) of an amorphous compound. Reverse phase HP of this compound
LC (Inertsil ODS-2, 6 x 150mm, A: 0.1M TEAA (pH 7.
0), B: acetonitrile, B / (A + B) = 0.32, 1ml / min, 60
It was eluted at 6.62 min when analyzed at 260 ° C.
【０２２１】UVmax(H2O)：256 nmUVmax (H 2 O): 256 nm
【０２２２】[0222]
【実施例８】Example 8
【０２２３】[0223]
【化２５】 [Chemical 25]
【０２２４】５００Å コントロールドポアグラス（CP
G ）充てん剤であるG-CPG （３０μｍｏｌ、８７０ｍ
ｇ）に対し、Ａ−Ｈ−ホスホネート カップリングとＧ
−Ｈ−ホスホネート カップリングを２回、順に行っ
た。500Å Controlled pore glass (CP
G) G-CPG as a packing material (30 μmol, 870 m
g) to A-H-phosphonate coupling and G
The -H-phosphonate coupling was performed twice in sequence.
【０２２５】Ｈ−ホスホネート カップリングが終了し
た後、担体（２９０ｍｇ、１０μｍｏｌ）に１０％メト
キシエチルアミン／四塩化炭素溶液を２ｍｌ加え、室温
で３０分間放置後、アセトニトリルで洗浄した。After the H-phosphonate coupling was completed, 2 ml of 10% methoxyethylamine / carbon tetrachloride solution was added to the carrier (290 mg, 10 μmol), left at room temperature for 30 minutes, and then washed with acetonitrile.
【０２２６】この担体と実施例１ｃのＤＮＡ／ＲＮＡシ
ンセサイザーを用いて、実施例１ｃと同様にＤＮＡ鎖を
伸長した。但し、ＴＧＧという塩基配列を入力し、TETD
／アセトニトリル溶液を用いた硫化反応は行わず、酸化
溶液（ヨウ素溶液）による酸化反応を行った。精製にお
いては、逆相HPLC（Inertsil PREP-ODS, 20 x 250 mm,
A:0.1 M TEAA (pH 7.0), B: アセトニトリル, 7ml/min,
B/(A+B)=0.32, 260nm）を行い、19.9分に溶出する分
画を集めた。減圧下にアセトニトリルを留去したのちに
凍結乾燥し、水に溶かして再度凍結乾燥して、アモルフ
ァス状の化合物を3.4 OD(260nm) 得た。本化合物を逆相
HPLC（Inertsil ODS-2, 6 x 150mm, A:0.1 M TEAA （pH
7.0）, B:アセトニトリル, B/(A+B)=0.32, 1ml/min, 6
0 ℃, 260 nm）で分析すると6.95min に溶出された。Using this carrier and the DNA / RNA synthesizer of Example 1c, the DNA chain was extended in the same manner as in Example 1c. However, enter the base sequence TGG, and
The sulfurization reaction using the / acetonitrile solution was not performed, and the oxidation reaction was performed using the oxidizing solution (iodine solution). For purification, reverse-phase HPLC (Inertsil PREP-ODS, 20 x 250 mm,
A: 0.1 M TEAA (pH 7.0), B: Acetonitrile, 7ml / min,
B / (A + B) = 0.32, 260 nm) was performed and the fractions eluting at 19.9 minutes were collected. After distilling off acetonitrile under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to obtain 3.4 OD (260 nm) of an amorphous compound. Reverse phase of this compound
HPLC (Inertsil ODS-2, 6 x 150mm, A: 0.1 M TEAA (pH
7.0), B: Acetonitrile, B / (A + B) = 0.32, 1ml / min, 6
It was eluted at 6.95 min when analyzed at 0 ° C and 260 nm).
【０２２７】UVmax(H2O)：255 nmUVmax (H 2 O): 255 nm
【０２２８】[0228]
【実施例９】[Example 9]
【０２２９】[0229]
【化２６】 [Chemical formula 26]
【０２３０】５００Å コントロールドポアグラス（CP
G ）充てん剤であるG-CPG （３０μｍｏｌ、８７０ｍ
ｇ）に対し、Ａ−Ｈ−ホスホネート カップリングとＧ
−Ｈ−ホスホネート カップリングを３回、順に行っ
た。500Å Controlled pore glass (CP
G) G-CPG as a packing material (30 μmol, 870 m
g) to A-H-phosphonate coupling and G
The -H-phosphonate coupling was performed three times in sequence.
【０２３１】Ｈ−ホスホネート カップリングが終了し
た後、担体（２９０ｍｇ、１０μｍｏｌ）に１０％メト
キシエチルアミン／四塩化炭素溶液を２ｍｌ加え、室温
で３０分間放置後、アセトニトリルで洗浄した。After completion of the H-phosphonate coupling, 2 ml of 10% methoxyethylamine / carbon tetrachloride solution was added to the carrier (290 mg, 10 μmol), left at room temperature for 30 minutes, and then washed with acetonitrile.
【０２３２】この担体と実施例１ｃのＤＮＡ／ＲＮＡシ
ンセサイザーを用いて、実施例１ｃと同様にＤＮＡ鎖を
伸長した。但し、ＴＧという塩基配列を入力し、TETD／
アセトニトリル溶液を用いた硫化反応は行わず、酸化溶
液（ヨウ素溶液）による酸化反応を行った。精製におい
ては、逆相HPLC（Inertsil PREP-ODS, 20 x 250 mm,A:
0.1 M TEAA (pH 7.0), B: アセトニトリル, 7ml/min,
B/(A+B)=0.32, 260 nm）を行い、18.0分に溶出する分画
を集めた。減圧下にアセトニトリルを留去したのちに凍
結乾燥し、水に溶かして再度凍結乾燥して、アモルファ
ス状の化合物を2.8 OD(260nm) 得た。本化合物を逆相HP
LC（Inertsil ODS-2, 6 x 150mm, A:0.1M TEAA （pH 7.
0）, B:アセトニトリル, B/(A+B)=0.32, 1ml/min, 60
℃, 260nm）で分析すると8.09min に溶出された。Using this carrier and the DNA / RNA synthesizer of Example 1c, the DNA chain was extended in the same manner as in Example 1c. However, enter the base sequence TG and enter TETD /
The sulfurization reaction using an acetonitrile solution was not performed, but the oxidation reaction was performed using an oxidizing solution (iodine solution). For purification, reverse phase HPLC (Inertsil PREP-ODS, 20 x 250 mm, A:
0.1 M TEAA (pH 7.0), B: Acetonitrile, 7ml / min,
B / (A + B) = 0.32, 260 nm) was performed and the fractions eluting at 18.0 minutes were collected. After the acetonitrile was distilled off under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to obtain 2.8 OD (260 nm) of an amorphous compound. Reverse phase HP of this compound
LC (Inertsil ODS-2, 6 x 150mm, A: 0.1M TEAA (pH 7.
0), B: acetonitrile, B / (A + B) = 0.32, 1ml / min, 60
It was eluted at 8.09 min when analyzed at 260 ° C.
【０２３３】UVmax(H2O)：256 nmUVmax (H 2 O): 256 nm
【０２３４】[0234]
【実施例１０】Example 10
【０２３５】[0235]
【化２７】 [Chemical 27]
【０２３６】ミリジェン／バイオサーチ（日本ミリポア
・リミテッド社製）のCycloneTM Plus DNA/RNA シンセ
サイザーに、付属する合成用試薬類と、合成用のプログ
ラムとして15.0μmoleアミダイトカ−トリッジを接続し
た。ただしこのとき、チミジンに対応するβ−シアノエ
チルアミダイト溶液のかわりに、３５mMに調製した実施
例１ｂの化合物のアセトニトリル溶液を用い、またアデ
ノシンに対応するβ−シアノエチルアミダイト溶液のか
わりに、３５mMに調製したdA-Me Phosphonamidite (Gle
n Reseach)のアセトニトリル溶液を用い、固相担体とし
ては、５００オングストロング コントロールドポアグ
ラス（CPG ）充てん剤で３４μmol/g のG-CPG を１１８
mg（４μmol ）はかりとり、15.0μmol 用エンプティー
カラムにつめて使用した。ＴＧＧＧＡＧという塩基配列
を入力し、最後のＴを結合させた後には酸処理を行わな
い設定のプログラムを作動させた。この操作により、Ｃ
ＰＧ上に保護されたオリゴヌクレオチドが構築された誘
導体を得た。これを減圧下乾燥したのちにカラムからと
り出し、２ｍｌのエタノール／アセトニトリル／２９％
アンモニア水（45:45:10 v/v/v）にひたして密閉し、室
温で約30分間反応した。その溶液に２ｍｌのエチレンジ
アミン１水和物を加え、室温で６時間放置した。CPG を
ろ過により除き、２ｍｌの５０％アセトニトリル水で２
回洗浄後、３０ｍｌの水で洗浄した。ろ液と洗浄液を合
わせた液に対して１０％アセトニトリルを含む６Ｎ塩酸
を用いて氷冷下中和した。これを逆相カラムクロマトグ
ラフィー（Preparative C18, Waters, 1.5 x 15 cm, 50
mM 炭酸水素トリエチルアミン水溶液 (TEAB),及びア
セトニトリル, 10-50%CH3CN-TEAB linear gradient, 25
4 nm）で精製し、アモルファス状の化合物を89 OD(260n
m)得た。本化合物を逆相HPLC（Inertsil ODS-2, 6 x 15
0mm, A:5% アセトニトリル−0.1 M 酢酸トリエチルアミ
ン水溶液（TEAA, pH 7.0）, B:アセトニトリル, B/(A+
B)=0.28, 1ml/min,60 ℃, 260 nm）で分析すると7.85 m
inに溶出された。A Cyclone ™ Plus DNA / RNA synthesizer manufactured by Milligen / Biosearch (manufactured by Japan Millipore Limited) was connected with attached reagents for synthesis and 15.0 μmole amidite cartridge as a program for synthesis. However, at this time, the acetonitrile solution of the compound of Example 1b adjusted to 35 mM was used in place of the β-cyanoethylamidite solution corresponding to thymidine, and the β-cyanoethylamidite solution corresponding to adenosine was adjusted to 35 mM. dA-Me Phosphonamidite (Gle
n Reseach) in acetonitrile, and as a solid-phase carrier, 500 μg of Strong Controlled Poregrass (CPG) packing material containing 34 μmol / g of G-CPG.
mg (4 μmol) was weighed and used by filling an empty column for 15.0 μmol. After inputting the base sequence TGGGAG and binding the last T, a program was set up so that no acid treatment was performed. By this operation, C
A derivative in which a protected oligonucleotide was constructed on PG was obtained. This was dried under reduced pressure and then removed from the column, and 2 ml of ethanol / acetonitrile / 29%
It was immersed in aqueous ammonia (45:45:10 v / v / v), sealed, and reacted at room temperature for about 30 minutes. 2 ml of ethylenediamine monohydrate was added to the solution, and the mixture was allowed to stand at room temperature for 6 hours. Remove CPG by filtration and add 2 ml of 50% aqueous acetonitrile to
After washing twice, it was washed with 30 ml of water. The combined solution of the filtrate and the washing solution was neutralized with 6N hydrochloric acid containing 10% acetonitrile under ice cooling. Reversed phase column chromatography (Preparative C18, Waters, 1.5 x 15 cm, 50
mM Triethylamine bicarbonate aqueous solution (TEAB), and acetonitrile, 10-50% CH 3 CN-TEAB linear gradient, 25
4 nm) and the amorphous compound was converted to 89 OD (260n
m) Got it. This compound was purified by reverse phase HPLC (Inertsil ODS-2, 6 x 15
0mm, A: 5% acetonitrile-0.1 M triethylamine acetate aqueous solution (TEAA, pH 7.0), B: acetonitrile, B / (A +
B) = 0.28, 1 ml / min, 60 ℃, 260 nm) 7.85 m
Eluted in.
【０２３７】UVmax(H2O)：２５５ ｎｍUVmax (H 2 O): 255 nm
【０２３８】[0238]
【実施例１１】[Embodiment 11]
【０２３９】[0239]
【化２８】 [Chemical 28]
【０２４０】以下の操作を除き、実施例１０と同様にし
て実施例１１の化合物を合成した。シチジンに対応する
β−シアノエチルアミダイト溶液のかわりに、３５ｍＭ
に調製したdeoxyguanosine (N-iBu) methyl phosphonam
idite (American Bionetic Inc.)のテトラヒドロフラン
溶液を用い、ＴＧＧＣＡＧという塩基配列を入力した。
また、精製においては、逆相カラムクロマトグラフィー
（Preparative C18, Waters, 1.5 x 15 cm,50 mM TEAB,
アセトニトリル, 10-50%CH3CN-TEAB linear gradient,
254 nm ）を行い、アモルファス状の化合物を90 OD(26
0nm)得た。本化合物を逆相HPLC（Inertsil ODS-2, 6 x
150mm, A:0.1 M TEAA （pH 7.0）, B:アセトニトリル,
B/(A+B)=0.28, 1ml/min, 60 ℃, 260 nm）で分析すると
8.27 minに溶出された。The compound of Example 11 was synthesized in the same manner as Example 10 except for the following operations. 35 mM instead of β-cyanoethylamidite solution corresponding to cytidine
Prepared deoxyguanosine (N-iBu) methyl phosphonam
Using a tetrahydrofuran solution of idite (American Bionetic Inc.), a base sequence called TGGCAG was input.
For purification, reverse phase column chromatography (Preparative C18, Waters, 1.5 x 15 cm, 50 mM TEAB,
Acetonitrile, 10-50% CH 3 CN-TEAB linear gradient,
254 nm) to convert the amorphous compound to 90 OD (26
0 nm) was obtained. This compound was analyzed by reverse phase HPLC (Inertsil ODS-2, 6 x
150mm, A: 0.1 M TEAA (pH 7.0), B: Acetonitrile,
B / (A + B) = 0.28, 1ml / min, 60 ℃, 260nm)
It was eluted at 8.27 min.
【０２４１】UVmax(H2O)：255 nmUVmax (H 2 O): 255 nm
【０２４２】[0242]
【実施例１２】[Example 12]
【０２４３】[0243]
【化２９】 [Chemical 29]
【０２４４】以下の操作を除き、実施例１０と同様にし
て実施例１２の化合物を合成した。すなわち、シチジン
に対応するβ−シアノエチルアミダイト溶液のかわり
に、３５mMに調製したdeoxyguanosine (N-iBu) methyl
phosphonamidite (American Bionetic Inc.)のテトラヒ
ドロフラン溶液を用い、ＴＧＣＣＡＧという塩基配列を
入力した。また、精製においては、逆相カラムクロマト
グラフィー（Preparative C18, Waters, 1.5 x 15 cm,5
0 mM TEAB 及びアセトニトリル, 10-50%CH3CN-TEAB lin
ear gradient, 254 nm）を行い、アモルファス状の化合
物を53 OD(260nm)得た。本化合物を逆相HPLC（Inertsil
ODS-2, 6 x 150mm, A:0.1 M TEAA （pH 7.0）, B:アセ
トニトリル, B/(A+B)=0.28, 1ml/min, 60 ℃, 260 nm）
で分析すると8.44, 8.65 min（面積比53:47 ）にメチル
ホスホネ−トの不斉により分離して溶出された。The compound of Example 12 was synthesized in the same manner as Example 10 except for the following operations. That is, instead of the β-cyanoethylamidite solution corresponding to cytidine, deoxyguanosine (N-iBu) methyl prepared at 35 mM was prepared.
Using a tetrahydrofuran solution of phosphonamidite (American Bionetic Inc.), a base sequence called TGCCAG was input. For purification, reverse-phase column chromatography (Preparative C18, Waters, 1.5 x 15 cm, 5
0 mM TEAB and acetonitrile, 10-50% CH 3 CN-TEAB lin
Ear gradient, 254 nm) was performed to obtain 53 OD (260 nm) of an amorphous compound. This compound was analyzed by reverse phase HPLC (Inertsil
ODS-2, 6 x 150mm, A: 0.1 M TEAA (pH 7.0), B: acetonitrile, B / (A + B) = 0.28, 1ml / min, 60 ℃, 260 nm)
When analyzed by (4), it was separated and eluted at 8.44, 8.65 min (area ratio 53:47) due to asymmetry of methylphosphonate.
【０２４５】UVmax(H2O)：256 nmUVmax (H 2 O): 256 nm
【０２４６】[0246]
【実施例１３】Example 13
【０２４７】[0247]
【化３０】 [Chemical 30]
【０２４８】以下の操作を除き、実施例１０と同様にし
て実施例１３の化合物を合成した。すなわち、シチジン
に対応するβ−シアノエチルアミダイト溶液のかわり
に、３５mMに調製したdeoxyguanosine (N-iBu) methyl
phosphonamidite (American Bionetic Inc.)のテトラヒ
ドロフラン溶液を用い、ＴＣＣＣＡＧという塩基配列を
入力した。また、精製においては、逆相カラムクロマト
グラフィー（Preparative C18, Waters, 1.5 x 15 cm,5
0 mM TEAB 及びアセトニトリル, 10-50%CH3CN-TEAB li
near gradient, 254 nm ）を行い、アモルファス状の化
合物を87 OD(260nm)得た。本化合物を逆相HPLC（Inerts
il ODS-2, 6 x 150mm, A:0.1 M TEAA （pH7.0）, B:ア
セトニトリル, B/(A+B)=0.28, 1ml/min, 60 ℃, 260 n
m）で分析すると9.23, 9.58, 10.35, 11.04, 11.38 min
（面積比32:28:29:7:4）にメチルホスホネ−トの不斉
により分離して溶出された。The compound of Example 13 was synthesized in the same manner as Example 10 except for the following operations. That is, instead of the β-cyanoethylamidite solution corresponding to cytidine, deoxyguanosine (N-iBu) methyl prepared at 35 mM was prepared.
Using a tetrahydrofuran solution of phosphonamidite (American Bionetic Inc.), a base sequence called TCCCAG was input. For purification, reverse-phase column chromatography (Preparative C18, Waters, 1.5 x 15 cm, 5
0 mM TEAB and acetonitrile, 10-50% CH 3 CN-TEAB li
near gradient, 254 nm) was performed to obtain 87 OD (260 nm) of an amorphous compound. This compound was analyzed by reverse phase HPLC (Inerts
il ODS-2, 6 x 150mm, A: 0.1 M TEAA (pH7.0), B: acetonitrile, B / (A + B) = 0.28, 1ml / min, 60 ℃, 260 n
m) is 9.23, 9.58, 10.35, 11.04, 11.38 min
(Area ratio 32: 28: 29: 7: 4) was separated and eluted due to asymmetry of methylphosphonate.
【０２４９】UVmax(H2O)：256 nmUVmax (H 2 O): 256 nm
【０２５０】[0250]
【実施例１４】 （１４ａ）Ｏ−ジメトキシトリチル エチレングリコー
ル エチレングリコール ３．１ｇ（５０ｍｍｏｌ）をピリ
ジンに溶解、留去して、乾燥した。そこへ、ピリジン
（４０ｍｌ）を加え、溶解し、４、４’ージメトキシト
リチルクロライド ３．３８ｇ（１０ｍｍｏｌ）を加
え、室温で２時間攪拌した。原料の消失をＴＬＣで確認
後、メタノ−ル（５ｍｌ）を加えて、約半分程度まで濃
縮した。これに塩化メチレン（１００ｍｌ）を加え、飽
和重曹水で洗浄し、有機層を１ＰＳ（ワットマン）ろ過
後、溶媒を留去した。この残渣をシリカゲルカラムクロ
マトグラフィ−（７０−２３０ｍｅｓｈ、１００ｇ、１
％メタノール／塩化メチレン）で精製し、ガム状の１．
９７ｇの目的化合物を得た。Example 14 (14a) O-dimethoxytrityl ethylene glycol
Le ethylene glycol dissolved 3.1g of (50 mmol) in pyridine and evaporated, and dried. Pyridine (40 ml) was added thereto, dissolved, 4,4′-dimethoxytrityl chloride 3.38 g (10 mmol) was added, and the mixture was stirred at room temperature for 2 hours. After confirming the disappearance of the raw materials by TLC, methanol (5 ml) was added and the mixture was concentrated to about half. Methylene chloride (100 ml) was added to this, and the mixture was washed with saturated aqueous sodium hydrogen carbonate, the organic layer was filtered by 1PS (Whatman), and the solvent was evaporated. This residue was subjected to silica gel column chromatography (70-230 mesh, 100 g, 1
% Methanol / methylene chloride) to give a gum-like 1.
97 g of the target compound are obtained.
【０２５１】1H-NMR(270MHz、CDCl3 、TMS) δppm: 7.4
5-6.82(13H,m,Ph),3.79(6H,S,CH3-)、3.75(2H,t,CH2OH,J
=4.95Hz)、3.25(2H,t, DMT-O-CH2-、J=4.62Hz)、1.95(1H,
t,OH) （１４ｂ） 1 H-NMR (270 MHz, CDCl 3 , TMS) δppm: 7.4
5-6.82 (13H, m, Ph), 3.79 (6H, S, CH 3- ), 3.75 (2H, t, CH 2 OH, J
= 4.95Hz), 3.25 (2H, t, DMT-O-CH 2- , J = 4.62Hz), 1.95 (1H,
t, OH) (14b)
【０２５２】[0252]
【化３１】 [Chemical 31]
【０２５３】実施例１４ａの化合物 ０．１８ｇ
（０．５ｍｍｏｌ）をピリジンに溶解、留去して、乾燥
した。そこへ、塩化メチレン（２ｍｌ）を加え、溶解
し、無水コハク酸７５ｍｇ（０．７５ｍｍｏｌ）とジメ
チルアミノピリジン９２ｍｇ （０．７５ｍｍｏｌ）を
加え、１時間攪拌した。反応の終了をＴＬＣで確認後、
塩化メチレンで希釈し、０. ５Ｍ ＫＨ2 ＰＯ4 （ｐＨ
５. ０）、水の順に洗浄し、有機層を硫酸ナトリウム
（無水）で乾燥した。溶媒を留去し、Ｏ−ジメトキシト
リチル エチレングリコール モノサクシネ−トとし
た。0.18 g of the compound of example 14a
(0.5 mmol) was dissolved in pyridine, evaporated, and dried. Methylene chloride (2 ml) was added to and dissolved therein, 75 mg (0.75 mmol) of succinic anhydride and 92 mg (0.75 mmol) of dimethylaminopyridine were added, and the mixture was stirred for 1 hour. After confirming the completion of the reaction by TLC,
Dilute with methylene chloride and add 0.5M KH 2 PO 4 (pH
5.0) and then washed with water, and the organic layer was dried over sodium sulfate (anhydrous). The solvent was distilled off to obtain O-dimethoxytrityl ethylene glycol monosuccinate.
【０２５４】さらにピリジンを加えて、留去し、乾燥し
た後、ジメチルホルムアミド（３ｍｌ）に溶解し、ペン
タクロロフェノール ０．１６ｇ（０．７５ｍｍｏ
ｌ）、１，３−ジシクロヘキシルカルボジイミド ０．
１６ｇ （０．７５ｍｍｏｌ）を加え、室温で４２時間
攪拌した。析出した不溶物を濾別し、濾液の溶媒を留去
した。残渣にベンゼンを加え、再び析出した不溶物を濾
別し、濾液の溶媒を留去した。Pyridine was further added, the mixture was distilled off, dried and then dissolved in dimethylformamide (3 ml) to give 0.16 g (0.75 mmo) of pentachlorophenol.
l), 1,3-dicyclohexylcarbodiimide 0.
16 g (0.75 mmol) was added, and the mixture was stirred at room temperature for 42 hours. The precipitated insoluble material was filtered off, and the solvent of the filtrate was distilled off. Benzene was added to the residue, the insoluble material deposited again was filtered off, and the solvent in the filtrate was distilled off.
【０２５５】この残渣のうちの ０．２５ｇ （０．２
ｍｍｏｌ）を、ジメチルホルムアミド（４ｍｌ）に溶解
し、トリエチルアミン ６０μｌ（０．４４ｍｍｏｌ）
とアミノプロピルーＣＰＧ（２．０ｇ、アミノ基が０．
１２９ｍｍｏｌ／ｇ量、導入されている）を加え、室温
で３６時間放置した。ＣＰＧ担体を濾取し、塩化メチレ
ンで洗浄後、減圧乾燥した。このＣＰＧ担体にキャップ
Ａ，Ｂ溶液（日本ミリポア・リミテッド）を各１０ｍｌ
加え、１０分間放置し、未反応のアミノ基をアセチル化
した。ピリジン、塩化メチレンの順で洗浄し減圧乾燥
し、化合物（１４ｂ）を得た。Of this residue, 0.25 g (0.2
mmol) in dimethylformamide (4 ml) and triethylamine 60 μl (0.44 mmol)
And aminopropyl-CPG (2.0 g, the amino group is less than 0.
(129 mmol / g amount, introduced) was added and left at room temperature for 36 hours. The CPG carrier was collected by filtration, washed with methylene chloride, and dried under reduced pressure. 10 ml each of Cap A and B solutions (Japan Millipore Limited) are added to this CPG carrier.
In addition, the mixture was allowed to stand for 10 minutes to acetylate unreacted amino groups. It was washed with pyridine and methylene chloride in this order and dried under reduced pressure to obtain the compound (14b).
【０２５６】実施例１４ｂの化合物へのＯ−ジメトキシ
トリチル エチレングリコールの導入量を、次の方法で
定量した。実施例１２ｂの化合物９．６ｍｇを、これに
デブロック溶液（ジクロロ酢酸ー塩化メチレン溶液、日
本ミリポア・リミテッド）を加え、３分程振とうし、塩
化メチレンで全量を２０ｍｌとした。そのうち０. ４ｍ
ｌを試験管にとり、溶媒を留去後、過塩素酸ーエタノー
ル（３：２ｖ／ｖ）溶液（３ｍｌ）を加え、５００ｎｍ
におけるジメトキシトリチルカチオンの吸光度を測定し
た（ε＝７１７００）。The amount of O-dimethoxytrityl ethylene glycol introduced into the compound of Example 14b was quantified by the following method. A deblocking solution (dichloroacetic acid-methylene chloride solution, Japan Millipore Limited) was added to the compound of Example 12b (9.6 mg), and the mixture was shaken for about 3 minutes to a total volume of 20 ml with methylene chloride. 0.4m of which
After taking 1 to a test tube and distilling off the solvent, a perchloric acid-ethanol (3: 2 v / v) solution (3 ml) was added, and 500 nm was added.
The absorbance of the dimethoxytrityl cation was measured (ε = 71700).
【０２５７】 ジメトキシトリチル基の導入量＝４０．０μｍｏｌ／ｇ （１４ｃ）Introduction amount of dimethoxytrityl group = 40.0 μmol / g (14c)
【０２５８】[0258]
【化３２】 [Chemical 32]
【０２５９】ミリジェン／バイオサーチ（日本ミリポア
・リミテッド社製）のCycloneTM Plus DNA/RNA シンセ
サイザーに、付属する合成用試薬類と、合成用のプログ
ラムとして15.0μmoleアミダイトカ−トリッジを接続し
た。ただしこのとき、チミジンに対応するβ−シアノエ
チルアミダイト溶液のかわりに、３５mMに調製した実施
例１ｂの化合物のアセトニトリル溶液を用い、固相担体
としては、実施例１４ｂの化合物を１２５mg（５μmol
）分はかりとり、15.0μmol 用エンプティーカラムに
つめて使用した。ＴＧＧＧＡＧＸという塩基配列を入力
し、最後のＴを結合させた後には酸処理を行わない設定
のプログラムを作動させた。但し、２回目のカップリン
グでＡ−ベータアミダイトを反応させた後と４回目のカ
ップリングでＧ−ベータアミダイトを反応させた後は、
酸化溶液（ヨウ素溶液）で酸化せずに、シンセサイザー
からカラムを取り外し、５ｍｌのTETD／アセトニトリル
溶液をカラムに入れ、室温で１５分間放置した。アセト
ニトリルで洗浄し、再びシンセサイザーに取り付けた。
この操作により、ＣＰＧ上に保護されたオリゴヌクレオ
チドが構築された誘導体を得た。これを減圧下乾燥した
のちにカラムからとり出し、約１０ｍｌの２９％アンモ
ニア水にひたして密閉し、室温で約２日間反応した。CP
G をろ過により除き、１０ｍｌの水で２回洗浄した。ろ
液と洗浄液を合わせて、１０ｍｌまで濃縮し、１０mLの
酢酸エチルで３回洗浄し、水溶液を約３ｍｌに濃縮し
た。これを逆相カラムクロマトグラフィー（Preparativ
e C18, Waters, 1.5 x 15 cm, 100 mM TEAB 及びアセト
ニトリル, 15-50%CH3CN-TEAB linear gradient, 254 n
m ）で粗精製した後、逆相HPLC（Inertsil PREP-ODS, 2
0 x250 mm, A:0.1 M TEAA (pH 7.0), B: アセトニトリ
ル, 7ml/min, B/(A+B)=0.27,260 nm ）を行い、50.20
分に溶出する分画を集めた。減圧下にアセトニトリルを
留去したのちに凍結乾燥し、水に溶かして再度凍結乾燥
して、アモルファス状の化合物を37 OD(260nm)得た。本
化合物を逆相HPLC（Inertsil ODS-2, 6 x 150mm, A:0.1
M TEAA,（pH 7.0）, B:アセトニトリル, B/(A+B)=0.2
6, 1ml/min, 60℃, 260 nm）で分析すると17.50minに溶
出された。A Cyclone ™ Plus DNA / RNA synthesizer manufactured by Milligen / Biosearch (manufactured by Japan Millipore Limited) was connected with attached reagents for synthesis and a 15.0 μmole amidite cartridge as a program for synthesis. However, at this time, instead of the β-cyanoethylamidite solution corresponding to thymidine, an acetonitrile solution of the compound of Example 1b adjusted to 35 mM was used, and 125 mg (5 μmol of 5 μmol of the compound of Example 14b was used as a solid phase carrier.
) Weighed aliquots, packed them in an empty column for 15.0 μmol, and used them. After inputting the base sequence of TGGGAGX and binding the last T, a program was set to perform no acid treatment. However, after reacting the A-beta amidite with the second coupling and after reacting the G-beta amidite with the fourth coupling,
The column was removed from the synthesizer without being oxidized with an oxidizing solution (iodine solution), 5 ml of TETD / acetonitrile solution was put into the column, and left at room temperature for 15 minutes. It was washed with acetonitrile and reattached to the synthesizer.
By this operation, a derivative in which a protected oligonucleotide was constructed on CPG was obtained. This was dried under reduced pressure, then taken out from the column, immersed in about 10 ml of 29% ammonia water and sealed, and reacted at room temperature for about 2 days. CP
G was removed by filtration and washed twice with 10 ml of water. The filtrate and the washing solution were combined, concentrated to 10 ml, washed 3 times with 10 mL of ethyl acetate, and the aqueous solution was concentrated to about 3 ml. Reverse phase column chromatography (Preparativ
e C18, Waters, 1.5 x 15 cm, 100 mM TEAB and acetonitrile, 15-50% CH 3 CN-TEAB linear gradient, 254 n
m), followed by reverse phase HPLC (Inertsil PREP-ODS, 2
0 x250 mm, A: 0.1 M TEAA (pH 7.0), B: Acetonitrile, 7 ml / min, B / (A + B) = 0.27,260 nm) and 50.20
Fractions eluting in minutes were collected. After distilling off acetonitrile under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to obtain 37 OD (260 nm) of an amorphous compound. This compound was analyzed by reverse phase HPLC (Inertsil ODS-2, 6 x 150mm, A: 0.1
M TEAA, (pH 7.0), B: Acetonitrile, B / (A + B) = 0.2
It was eluted at 17.50 min when analyzed at 6, 1 ml / min, 60 ° C, 260 nm).
【０２６０】UVmax(H2O)：254 nmUVmax (H 2 O): 254 nm
【０２６１】[0261]
【実施例１５】Example 15
【０２６２】[0262]
【化３３】 [Chemical 33]
【０２６３】以下の操作を除き、実施例１４と同様にし
て実施例１５の化合物を合成した。２回目のカップリン
グでＡ−ベータアミダイトを反応させた後のTETD／アセ
トニトリル溶液を用いた硫化反応は行わず、酸化溶液
（ヨウ素溶液）による酸化反応を行った。また、精製に
おいては、逆相カラムクロマトグラフィー（Preparativ
e C18, Waters, 1.5 x 15 cm, 100 mM TEAB,及びアセト
ニトリル、 15-50%CH3CN-TEAB linear gradient, 254 n
m ）で精製し、アモルファス状の化合物を53 OD(260nm)
得た。本化合物を逆相HPLC（Inertsil ODS-2, 6 x 150m
m, A:0.1 M TEAA,(pH 7.0 ）, B:アセトニトリル, B/(A
+B)=0.26, 1ml/min, 60 ℃, 260 nm）で分析すると17.2
8minに溶出された。The compound of Example 15 was synthesized in the same manner as Example 14 except for the following operations. The sulfurization reaction using the TETD / acetonitrile solution after reacting the A-beta amidite with the second coupling was not performed, but the oxidation reaction was performed using the oxidizing solution (iodine solution). For purification, reverse-phase column chromatography (Preparativ
e C18, Waters, 1.5 x 15 cm, 100 mM TEAB, and acetonitrile, 15-50% CH 3 CN-TEAB linear gradient, 254 n
m), and the amorphous compound is 53 OD (260 nm)
Obtained. This compound was purified by reverse phase HPLC (Inertsil ODS-2, 6 x 150m
m, A: 0.1 M TEAA, (pH 7.0), B: acetonitrile, B / (A
+ B) = 0.26, 1 ml / min, 60 ℃, 260 nm)
Eluted at 8 min.
【０２６４】UVmax(H2O)：254 ｎｍUVmax (H 2 O): 254 nm
【０２６５】[0265]
【実施例１６】Example 16
【０２６６】[0266]
【化３４】 Embedded image
【０２６７】以下の操作を除き、実施例１４と同様にし
て実施例１６の化合物を合成した。４回目のカップリン
グでＧ−ベータアミダイトを反応させた後のＴＥＴＤ／
アセトニトリル溶液を用いた硫化反応は行わず、酸化溶
液（ヨウ素溶液）による酸化反応を行った。また、精製
においては逆相カラムクロマトグラフィー（Preparativ
eC18, Waters, 1.5 x 15 cm, 100 mM TEAB, 20-30% ア
セトニトリル, linear gradient, 254 nm ）で粗精製し
た後、逆相HPLC（Inertsil PREP-ODS, 20 x 250 mm, A:
0.1 M TEAA (pH 7.0), B: アセトニトリル, 7ml/min, B
/(A+B)=0.27, 260 nm ）を行い、52.84 分に溶出する分
画を集めた。減圧下にアセトニトリルを留去したのちに
凍結乾燥し、水に溶かして再度凍結乾燥して、アモルフ
ァス状の化合物を57 OD(260nm)得た。本化合物を逆相HP
LC（Inertsil ODS-2, 6 x 150mm, A:0.1 M TEAA, （pH
7.0）, B:アセトニトリル, B/(A+B)=0.26, 1ml/min,室
温, 260 nm）で分析すると16.96minに溶出された。The compound of Example 16 was synthesized in the same manner as Example 14 except for the following operations. TETD / after reacting G-beta amidite with the fourth coupling
The sulfurization reaction using an acetonitrile solution was not performed, but the oxidation reaction was performed using an oxidizing solution (iodine solution). In addition, reverse phase column chromatography (Preparativ
After crude purification with eC18, Waters, 1.5 x 15 cm, 100 mM TEAB, 20-30% acetonitrile, linear gradient, 254 nm, reverse phase HPLC (Inertsil PREP-ODS, 20 x 250 mm, A:
0.1 M TEAA (pH 7.0), B: Acetonitrile, 7ml / min, B
/(A+B)=0.27, 260 nm) was performed and the fractions eluting at 52.84 minutes were collected. After distilling off acetonitrile under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to obtain 57 OD (260 nm) of an amorphous compound. Reverse phase HP of this compound
LC (Inertsil ODS-2, 6 x 150mm, A: 0.1 M TEAA, (pH
7.0), B: acetonitrile, B / (A + B) = 0.26, 1 ml / min, room temperature, 260 nm). It was eluted at 16.96 min.
【０２６８】UVmax(H2O)：255 ｎｍUVmax (H 2 O): 255 nm
【０２６９】[0269]
【実施例１７】Example 17
【０２７０】[0270]
【化３５】 Embedded image
【０２７１】以下の操作を除き、実施例１６と同様にし
て実施例１７の化合物を合成した。１回目のカップリン
グでＧ−ベータアミダイトを反応させた後は、酸化溶液
（ヨウ素溶液）で酸化せずに、シンセサイザーからカラ
ムを取り外し、５ｍｌのＴＥＴＤ／アセトニトリル溶液
をカラムに入れ、室温で１５分間放置した。アセトニト
リルで洗浄し、再びシンセサイザーに取り付けた。ま
た、精製においては、逆相HPLC（Inertsil PREP-ODS, 2
0 x 250 mm, A:0.1 M TEAA (pH 7.0), B: アセトニトリ
ル, 7ml/min, B/(A+B)=0.27, 260 nm ）を行い、19.32
分に溶出する分画を集めた。減圧下にアセトニトリルを
留去したのちに凍結乾燥し、水に溶かして再度凍結乾燥
して、アモルファス状の化合物を39 OD(260nm)得た。本
化合物を逆相HPLC（Inertsil ODS-2, 6 x 150mm, A:0.1
M TEAA, （pH 7.0）, B:アセトニトリル, B/(A+B)=0.
26, 1ml/min,室温, 260 nm）で分析すると18.79minに溶
出された。The compound of Example 17 was synthesized in the same manner as Example 16 except for the following operations. After reacting the G-beta amidite with the first coupling, the column was removed from the synthesizer without being oxidized with an oxidizing solution (iodine solution), 5 ml of TETD / acetonitrile solution was put into the column, and the mixture was allowed to stand at room temperature for 15 minutes. I left it. It was washed with acetonitrile and reattached to the synthesizer. For purification, reverse-phase HPLC (Inertsil PREP-ODS, 2
0 x 250 mm, A: 0.1 M TEAA (pH 7.0), B: Acetonitrile, 7 ml / min, B / (A + B) = 0.27, 260 nm) and then 19.32.
Fractions eluting in minutes were collected. After distilling off acetonitrile under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to obtain 39 OD (260 nm) of an amorphous compound. This compound was analyzed by reverse phase HPLC (Inertsil ODS-2, 6 x 150mm, A: 0.1
M TEAA, (pH 7.0), B: Acetonitrile, B / (A + B) = 0.
It was eluted at 18.79 min when analyzed at 26, 1 ml / min, room temperature, 260 nm).
【０２７２】UVmax(H2O)：255 nmUVmax (H 2 O): 255 nm
【０２７３】[0273]
【実施例１８】 （１８ａ）５’−Ｏ−トリチルーＮーベンゾイルー２’
ーデオキシシチジン Ｎーベンゾイルー２’ーデオキシシチジン ３．３１ｇ
（１０ｍｍｏｌ、（株）同人化学研究所）をピリジン２
５ｍｌに懸濁し、トリチルクロライド３．０７ｇ（１１
ｍｍｏｌ）を加え、１００℃、１時間撹拌した。室温に
戻し、溶媒を留去後、残渣に酢酸エチルと飽和重曹水を
加え分液した。有機層を飽和食塩水で２回洗浄し、無水
硫酸マグネシウムで乾燥した。溶媒を留去し、残渣をシ
リカゲルカラム（Lober column Si60, Size C ）にアプ
ライし、２−５％メタノール−塩化メチレンで溶出させ
ることにより１．４７ｇ（２６％）の目的化合物を得
た。1H-NMR(270MHz、CDCl3、TMS) δppm:8.72(1H, bs, N
H), 8.26(1H,d,H5,J=7.3Hz),7.89(1H,d,H6,J=7.3Hz),
7.64-7.26(20H,m,Ph), 6.29(1H,t,H1',J=5.9Hz), 4.53-
4.48(1H,m,H3'), 4.16-4.12(1H,m,H4'), 3.57-3.42(2H,
m,H5'), 2.77-2.67, 2.37-2.23(2H,m,H2'), 2.51(1H,b
r,OH) （１８ｂ）５’−Ｏ−トリチル−Ｎ−ベンゾイル−２’
−デオキシシチジン−３’−Ｏ−（２−シアノエチル
Ｎ，Ｎ−ジイソプロピル）ホスホロアミダイト 実施例１８ａの化合物 ４０２ｍｇ（０．７ｍｍｏｌ）
にピリジンを加え留去し乾燥後、塩化メチレン（３．５
ｍｌ）に溶解し、ジイソプロピルアンモニウムテトラゾ
リド６０ｍｇ（０．３５ｍｍｏｌ）を加え、アルゴン雰
囲気下、２ーシアノエチル Ｎ，Ｎ，Ｎ，Ｎ，−テトラ
イソプロピルアミノホスホロジアミダイト ２４５μｌ
（０．７７ｍｍｏｌ）を滴下した。室温で３．５時間撹
はんし、溶媒を留去した。残渣を酢酸エチルに溶解し、
１０％Na2CO3水、飽和食塩水で洗浄後、無水硫酸ナトリ
ウムで乾燥した。溶媒を留去し、残渣をシリカゲルカラ
ム（７０−２３０ｍｅｓｈ、２３ｇ、溶出液：酢酸エチ
ル）を行い精製し、あわ状物質として３３７ｍｇ（６２
％）の目的化合物を得た。Example 18 (18a) 5′-O-Trityl-N-benzoyl-2 ′
Over deoxycytidine N Benzoiru 2 'over deoxycytidine 3.31g
(10 mmol, Dojindo Laboratories Inc.) with pyridine 2
Suspended in 5 ml, 3.07 g of trityl chloride (11
mmol) was added and the mixture was stirred at 100 ° C. for 1 hour. After returning to room temperature and evaporating the solvent, ethyl acetate and saturated aqueous sodium hydrogen carbonate were added to the residue for partitioning. The organic layer was washed twice with saturated saline and dried over anhydrous magnesium sulfate. The solvent was evaporated, the residue was applied to a silica gel column (Lober column Si60, Size C) and eluted with 2-5% methanol-methylene chloride to obtain 1.47 g (26%) of the target compound. 1 H-NMR (270MHz, CDCl 3 , TMS) δppm: 8.72 (1H, bs, N
H), 8.26 (1H, d, H5, J = 7.3Hz), 7.89 (1H, d, H6, J = 7.3Hz),
7.64-7.26 (20H, m, Ph), 6.29 (1H, t, H1 ', J = 5.9Hz), 4.53-
4.48 (1H, m, H3 '), 4.16-4.12 (1H, m, H4'), 3.57-3.42 (2H,
m, H5 '), 2.77-2.67, 2.37-2.23 (2H, m, H2'), 2.51 (1H, b
r, OH) (18b) 5'-O-trityl-N-benzoyl-2 '
-Deoxycytidine-3'-O- (2-cyanoethyl
N, N-diisopropyl) phosphoramidite Example 18a compound 402 mg (0.7 mmol)
Pyridine was added to the mixture, the mixture was distilled off, and the residue was dried.
ml), diisopropylammonium tetrazolid 60 mg (0.35 mmol) was added, and under an argon atmosphere, 2-cyanoethyl N, N, N, N, -tetraisopropylaminophosphorodiamidite 245 μl
(0.77 mmol) was added dropwise. The mixture was stirred at room temperature for 3.5 hours, and the solvent was distilled off. Dissolve the residue in ethyl acetate,
The extract was washed with 10% Na 2 CO 3 water and saturated saline and then dried over anhydrous sodium sulfate. The solvent was evaporated, the residue was purified by silica gel column (70-230 mesh, 23 g, eluent: ethyl acetate), and 337 mg (62
%) Of the desired compound was obtained.
【０２７４】1H-NMR(270MHz、CDCl3、TMS) δppm:8.87(1
H, bs, NH), 8.52,8.43(1H,d,H5,J=7.3 Hz), 8.11(1H,
d,H6,J=7.3 Hz), 7.86-7.23(20H,m,Ph), 6.55-6.49(1H,
m,H1'),4.91-4.79(1H,m,H3'), 4.47-4.46(1H,m,H4'),
4.10-3.60(6H,m,H5', POCH2 andNCH), 3.08-2.46(4H,m,
H2' and CH2CN), 1.40-1.29(12H,m,CH3 of iPr) （１８ｃ） 1 H-NMR (270 MHz, CDCl 3 , TMS) δppm: 8.87 (1
H, bs, NH), 8.52, 8.43 (1H, d, H5, J = 7.3 Hz), 8.11 (1H,
d, H6, J = 7.3 Hz), 7.86-7.23 (20H, m, Ph), 6.55-6.49 (1H,
m, H1 '), 4.91-4.79 (1H, m, H3'), 4.47-4.46 (1H, m, H4 '),
4.10-3.60 (6H, m, H5 ', POCH 2 and NCH), 3.08-2.46 (4H, m,
H2 'and CH 2 CN), 1.40-1.29 (12H, m, CH 3 of iPr) (18c)
【０２７５】[0275]
【化３６】 Embedded image
【０２７６】ミリジェン／バイオサーチ（日本ミリポア
・リミテッド社製）のCycloneTM Plus DNA/RNA シンセ
サイザーに、付属する合成用試薬類と、合成用のプログ
ラムとして15.0μmoleアミダイトカ−トリッジを接続し
た。ただしこのとき、チミジンに対応するβ−シアノエ
チルアミダイト溶液のかわりに、３５mMに調製した実施
例１８ｂの化合物のアセトニトリル溶液を用い、固相担
体としては、実施例１４ｂの化合物を１２５mg（５μmo
l ）分はかりとり、15.0μmol 用エンプティーカラムに
つめて使用した。ＴＧＣＧＧＸという塩基配列を入力
し、最後のＴを結合させた後には酸処理を行わない設定
のプログラムを作動させた。但し、２回目のカップリン
グでＧ−ベータアミダイトを反応させた後は、酸化溶液
（ヨウ素溶液）で酸化せずに、シンセサイザーからカラ
ムを取り外し、５ｍｌのTETD／アセトニトリル溶液をカ
ラムに入れ、室温で１５分間放置した。アセトニトリル
で洗浄し、再びシンセサイザーに取り付けた。この操作
により、ＣＰＧ上に保護されたオリゴヌクレオチドが構
築された誘導体を得た。これを減圧下乾燥したのちにカ
ラムからとり出し、約１０ｍｌの２９％アンモニア水に
ひたして密閉し、室温で約２日間反応した。CPG をろ過
により除き、１０ｍｌの水で２回洗浄した。ろ液と洗浄
液を合わせて、１０ｍｌまで濃縮し、１０mLの酢酸エチ
ルで３回洗浄し、水溶液を約３ｍｌに濃縮した。これを
逆相HPLC（Inertsil PREP-ODS, 20 x 250 mm, A:0.1 M
TEAA (pH 7.0), B: アセトニトリル, 7ml/min, B%:10-6
0%(45min), 60 ℃, 260 nm）を行い、26.67 分に溶出す
る分画を集めた。減圧下にアセトニトリルを留去したの
ちに凍結乾燥し、水に溶かして再度凍結乾燥して、アモ
ルファス状の化合物を 65 OD(260nm) 得た。本化合物を
逆相HPLC（Inertsil ODS-2, 6 x 150mm, A:0.1 M TEAA,
（pH 7.0）, B:アセトニトリル, B%:10-60%(20min),
1ml/min, 60 ℃, 260 nm）で分析すると16.70 min に溶
出された。To the Cyclone ™ Plus DNA / RNA synthesizer of Milligen / Biosearch (manufactured by Japan Millipore Limited), the attached reagents for synthesis and 15.0 μmole amidite cartridge as a program for synthesis were connected. However, at this time, instead of the β-cyanoethylamidite solution corresponding to thymidine, an acetonitrile solution of the compound of Example 18b adjusted to 35 mM was used, and 125 mg (5 μmo of the compound of Example 14b was used as a solid phase carrier.
l) Weighed an aliquot and filled it in an empty column for 15.0 μmol before use. After inputting the base sequence TGCGGX and binding the last T, a program was set up so that no acid treatment was performed. However, after reacting the G-beta amidite with the second coupling, the column was removed from the synthesizer without being oxidized with an oxidizing solution (iodine solution), and 5 ml of TETD / acetonitrile solution was put into the column and allowed to stand at room temperature. Leave for 15 minutes. It was washed with acetonitrile and reattached to the synthesizer. By this operation, a derivative in which a protected oligonucleotide was constructed on CPG was obtained. This was dried under reduced pressure, then taken out from the column, immersed in about 10 ml of 29% ammonia water and sealed, and reacted at room temperature for about 2 days. CPG was removed by filtration and washed twice with 10 ml of water. The filtrate and the washing solution were combined, concentrated to 10 ml, washed 3 times with 10 mL of ethyl acetate, and the aqueous solution was concentrated to about 3 ml. Reversed phase HPLC (Inertsil PREP-ODS, 20 x 250 mm, A: 0.1 M
TEAA (pH 7.0), B: Acetonitrile, 7ml / min, B%: 10-6
0% (45 min), 60 ° C, 260 nm) was performed and the fractions eluting at 26.67 minutes were collected. After distilling off acetonitrile under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to obtain 65 OD (260 nm) of an amorphous compound. This compound was purified by reverse phase HPLC (Inertsil ODS-2, 6 x 150mm, A: 0.1 M TEAA,
(PH 7.0), B: Acetonitrile, B%: 10-60% (20min),
It was eluted at 16.70 min when analyzed at 1 ml / min, 60 ° C, 260 nm).
【０２７７】UVmax(H2O)：255 nmUVmax (H 2 O): 255 nm
【０２７８】[0278]
【実施例１９】Example 19
【０２７９】[0279]
【化３７】 Embedded image
【０２８０】以下の操作を除き、実施例１８ｃと同様に
して実施例１９の化合物を合成した。２回目のカップリ
ングでＧ−ベータアミダイトを反応させた後には、TETD
／アセトニトリル溶液を用いた硫化反応は行わず、酸化
溶液（ヨウ素溶液）による酸化反応を行い、３回目のカ
ップリングでＣ−ベータアミダイトを反応させた後に酸
化溶液（ヨウ素溶液）で酸化せずに、シンセサイザーか
らカラムを取り外し、５ｍｌのTETD／アセトニトリル溶
液をカラムに入れ、室温で１５分間放置した。アセトニ
トリルで洗浄し、再びシンセサイザーに取り付けた。ま
た、精製においては、逆相HPLC（Inertsil PREP-ODS, 2
0 x 250 mm, A:0.1 M TEAA (pH 7.0), B: アセトニトリ
ル, 7ml/min, B%:10-60%(30min), 60 ℃, 260 nm）を行
い、20.86 分に溶出する分画を集めた。減圧下にアセト
ニトリルを留去したのちに凍結乾燥し、水に溶かして再
度凍結乾燥して、アモルファス状の化合物を59 OD(260n
m)得た。本化合物を逆相HPLC（Inertsil ODS-2, 6 x 15
0mm, A:0.1 M TEAA, （pH7.0）, B:アセトニトリル, B
%:10-60%(20 min), 1ml/min, 60℃, 260 nm）で分析す
ると16.67 min に溶出された。The compound of Example 19 was synthesized in the same manner as Example 18c except for the following operations. After reacting G-beta amidite with the second coupling, TETD
/ Sulfurization reaction using acetonitrile solution is not carried out, oxidation reaction is carried out by oxidizing solution (iodine solution), and C-beta amidite is reacted by the third coupling, and then is not oxidized by oxidizing solution (iodine solution). Then, the column was removed from the synthesizer, 5 ml of the TETD / acetonitrile solution was put into the column, and left at room temperature for 15 minutes. It was washed with acetonitrile and reattached to the synthesizer. For purification, reverse-phase HPLC (Inertsil PREP-ODS, 2
0 x 250 mm, A: 0.1 M TEAA (pH 7.0), B: Acetonitrile, 7 ml / min, B%: 10-60% (30 min), 60 ° C, 260 nm) and elute at 20.86 minutes. Collected. After distilling off acetonitrile under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to give an amorphous compound at 59 OD (260n).
m) Got it. This compound was purified by reverse phase HPLC (Inertsil ODS-2, 6 x 15
0mm, A: 0.1 M TEAA, (pH7.0), B: Acetonitrile, B
%: 10-60% (20 min), 1 ml / min, 60 ° C, 260 nm) and it was eluted at 16.67 min.
【０２８１】UVmax(H2O)：255 ｎｍUVmax (H 2 O): 255 nm
【０２８２】[0282]
【実施例２０】Example 20
【０２８３】[0283]
【化３８】 [Chemical 38]
【０２８４】ＴＧＧＧＧＸという塩基配列を入力した操
作を除き、実施例１８ｃと同様にして実施例２０の化合
物を合成した。また、精製においては、逆相ＨＰＬＣ
（InertsilPREP-ODS, 20 x 250 mm, A:0.1 M TEAA (pH
7.0), B: アセトニトリル, 7ml/min, B%:10-60%(45mi
n), 60 ℃, 260 nm）を行い、25.0分に溶出する分画を
集めた。減圧下にアセトニトリルを留去したのちに凍結
乾燥し、水に溶かして再度凍結乾燥して、アモルファス
状の化合物を32 OD(260nm)得た。本化合物を逆相HPLC
（Inertsil ODS-2, 6 x 150mm, A:0.1 M TEAA, （pH
7.0）, B:アセトニトリル,B%:10-60%(20 min), 1ml/mi
n, 60℃, 260 nm）で分析すると16.60 min に溶出され
た。The compound of Example 20 was synthesized in the same manner as in Example 18c, except for the operation of inputting the base sequence TGGGGX. In the purification, reverse phase HPLC
(InertsilPREP-ODS, 20 x 250 mm, A: 0.1 M TEAA (pH
7.0), B: Acetonitrile, 7ml / min, B%: 10-60% (45mi
n), 60 ° C., 260 nm), and the fractions eluting at 25.0 minutes were collected. After distilling off acetonitrile under reduced pressure, the residue was freeze-dried, dissolved in water and freeze-dried again to obtain 32 OD (260 nm) of an amorphous compound. Reverse phase HPLC of this compound
(Inertsil ODS-2, 6 x 150mm, A: 0.1 M TEAA, (pH
7.0), B: Acetonitrile, B%: 10-60% (20 min), 1ml / mi
n, 60 ℃, 260 nm), it was eluted at 16.60 min.
【０２８５】UVmax(H2O)：254 nmUVmax (H 2 O): 254 nm
【０２８６】[0286]
【製剤例１】注射剤 1.5 重量% の実施例１６の化合物を、10容量% のプロピ
レングリコ−ル中で撹拌し、次いで、注射用水で一定容
量にした後、滅菌して製造した。[Formulation Example 1] Injectable preparation A compound was prepared by stirring 1.5% by weight of the compound of Example 16 in 10% by volume of propylene glycol, and then making up the solution to a fixed volume with water for injection followed by sterilization.
【０２８７】[0287]
【製剤例２】錠剤 上記のうち５）〜８）を混合し造粒した予製顆粒に、
１）〜４）を混合し粉砕したものを添加し、次いで打錠
機により打錠して１錠１００ｍｇの錠剤とした。[Formulation Example 2] Tablet Of the above, 5) to 8) were mixed and granulated into pre-made granules,
The ingredients 1) to 4) were mixed and pulverized, and then the mixture was tableted with a tableting machine to give 100 mg tablets.
【０２８８】[0288]
【製剤例３】カプセル剤 上記の１）〜５）を混合粉砕し，さらにふるいを通し、
よく混合したのち，常法に従いカプセル２００ｍｇのカ
プセル剤とした。[Formulation Example 3] Capsule The above 1) to 5) are mixed and crushed, and then passed through a sieve,
After mixing well, capsules of 200 mg were prepared according to a conventional method.
【０２８９】[0289]
【製剤例４】（ハ−ドカプセル剤） 標準二分式ハ−ドゼラチンカプセルの各々に、100 mgの
粉末状の実施例１６の化合物、150 mgのラクト−ス、50
mg のセルロ−ス及び6 mgのステアリン酸マグネシウム
を充填することにより、単位カプセルを製造し、洗浄
後、乾燥した。Formulation Example 4 (Hard Capsules) 100 mg of the compound of Example 16 in powder form, 150 mg of lactose, 50 in each of standard bisecting hard gelatin capsules.
Unit capsules were prepared by filling with mg cellulose and 6 mg magnesium stearate, washed and dried.
【０２９０】[0290]
【製剤例５】（ソフトカプセル剤） 消化性油状物、例えば、大豆油、綿実油又はオリ−ブ油
中に入れた、実施例１６の化合物の混合物を調製し、正
置換ポンプでゼラチン中に注入して、100 mgの活性成分
を含有するソフトカプセルを得、洗浄後、乾燥した。Formulation Example 5 (Soft Capsule) A mixture of the compounds of Example 16 in a digestible oil such as soybean oil, cottonseed oil or olive oil is prepared and injected into gelatin with a positive displacement pump. Thus, soft capsules containing 100 mg of active ingredient were obtained, washed, and dried.
【０２９１】[0291]
【製剤例６】（錠剤） 常法に従って、100 mgの実施例１６の化合物、0.2 mgの
コロイド性二酸化珪素、5 mgのステアリン酸マグネシウ
ム、275 mgの微結晶性セルロ−ス、11 mg のデンプン及
び98.8 mg のラクト−スを用いて製造した。[Formulation Example 6] (Tablets) According to a conventional method, 100 mg of the compound of Example 16, 0.2 mg of colloidal silicon dioxide, 5 mg of magnesium stearate, 275 mg of microcrystalline cellulose, and 11 mg of starch are used. And 98.8 mg of lactose.
───────────────────────────────────────────────────── フロントページの続き (72)発明者 金子 正勝 東京都品川区広町１丁目２番58号 三共株 式会社内 (72)発明者 大峰 寿典 東京都品川区広町１丁目２番58号 三共株 式会社内 (72)発明者 古川 秀比古 東京都品川区広町１丁目２番58号 三共株 式会社内 (72)発明者 西垣 隆 東京都品川区広町１丁目２番58号 三共株 式会社内 ─────────────────────────────────────────────────── ─── Continuation of the front page (72) Masakatsu Kaneko 1-25-2 Hiromachi, Shinagawa-ku, Tokyo Sankyo Co., Ltd. (72) Toshinori Omine 1-25-2 Hiromachi, Shinagawa-ku, Tokyo Sankyo stock company (72) Inventor Hidehiko Furukawa 1-2-58 Hiromachi, Shinagawa-ku, Tokyo Sankyo stock company (72) Takashi Nishigaki 1-2-58 Hiromachi, Shinagawa-ku, Tokyo Sankyo stock company
Claims (15)
Ｒ3 はそれぞれ独立に同一又は異なって水素原子、炭素
数１乃至４個のアルキル基、置換基を有していてもよい
アリール基又は置換基を有していてもよいアントラキノ
ニル基を示し、ＺはＣ又はＳｉを示すか、あるいは、Ｒ
2 、Ｒ3 及びＺが一緒になってフルオレニル基又はキサ
ンテニル基を示す。）を示し、Ｒ4 は水素原子、置換基
を有していてもよい炭素数１乃至４個のアルキル基、置
換基を有していてもよいアリール基又は置換基を有して
いてもよいアラルキル基、Ｙ1 、Ｙ3 及びＹ4 は同一又
は異なってＯ，Ｓ又はＮＨを示し、Ｙ2 はＯ，Ｓ，Ｎ
Ｈ、炭素数１乃至４個のアルキレン基又はフェニレン基
を示し、Ｘは水酸基で置換されていてもよい直鎖又は分
枝鎖の炭素数１乃至１０個のアルキレン基を示し、ｍ、
ｎは同一又は異なって０乃至１０の整数を示し、Ｂは鎖
長が３乃至９の部分的にホスホジエステル基がホスホロ
チオエート型ジエステル基、メチルホスホネート型ジエ
ステル基あるいはメトキシエチルアミノホスフェート型
ジエステル基に変換されたオリゴデオキシリボヌクレオ
チド（ＯＤＮ）を示す。但し、Ｂにおいて、各オリゴデ
オキシリボヌクレオチドの５’末端と３’末端の水酸基
は含まない］で表わされる化合物又はその塩。1. A general formula: [In the formula, Q is an R 1 R 2 R 3 Z group (in the formula, R 1 , R 2 and R 3 are independently the same or different and each represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a substituent group; Represents an optionally substituted aryl group or an optionally substituted anthraquinonyl group, Z represents C or Si, or R
2 , R 3 and Z together represent a fluorenyl group or a xanthenyl group. R 4 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms which may have a substituent, an aryl group which may have a substituent or a substituent which may have a substituent. Aralkyl groups, Y 1 , Y 3 and Y 4 are the same or different and represent O, S or NH, and Y 2 is O, S, N.
H represents an alkylene group having 1 to 4 carbon atoms or a phenylene group, X represents a linear or branched alkylene group having 1 to 10 carbon atoms which may be substituted with a hydroxyl group, and m,
n is the same or different and represents an integer of 0 to 10, and B is a partially phosphodiester group having a chain length of 3 to 9 converted to a phosphorothioate type diester group, a methylphosphonate type diester group or a methoxyethylaminophosphate type diester group. The prepared oligodeoxyribonucleotide (ODN) is shown. However, in B, the hydroxyl groups at the 5'end and 3'end of each oligodeoxyribonucleotide are not included] or a salt thereof.
ある化合物又はその塩。2. The compound according to claim 1, wherein the chain length of B is 4 to 8, or a salt thereof.
ある化合物又はその塩。3. The compound according to claim 1, wherein the chain length of B is 5 to 6, or a salt thereof.
されるオリゴデオキシリボヌクレオチドである化合物又
はその塩。 ［Ａ群］ＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧｅ
ＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，ＴｅＧｅＧｅＧｅ
ＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧＧ
ＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆＡｆＧ，ＴＧ
ｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧＧＧｇＡｇ
Ｇ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧ
ＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧ
Ｇ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧＧＡＧｅ
Ｇ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，ＴＧＣＧ
ＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧｆＧ，ｍ
ＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，ＧＧＧＣＧ
ＧＧｅＣ，ＴＡＧＧＡＧｅＧ，ＴＧＧＧＡＧＧｅＴ，Ｔ
ＧＧＧＣＧＣＡｅＧ，ＣＣｅＧ，ＴＣＧＧＡＧｅＧ，Ｔ
ＧｍＣＧＡＧｅＧ，ＧＴＧＧＧＡＧｅＧ，ＴＧｅＧ，Ｔ
ＧＧＧＡｍＧｅＧ，ＴＧＧＧＡＧｅＡ，ＡＡＴＧＧＧＡ
ＧｅＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧ
ｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧ
ｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧ
Ｇ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ，ＣＧＣｅＧＧ，Ｃ
ＧＧＧｅＴ，ＴＧＧＧｅＣ，ＴＧＧＧｅＴ（Ａ群中、Ａ
はアデニンデオキシリボヌクレオチド、Ｇはグアニンデ
オキシリボヌクレオチド、Ｃはシトシンデオキシリボヌ
クレオチド、Ｔはチミンデオキシリボヌクレオチド、ｍ
Ｃは５−メチルシトシンデオキシリボヌクレオチド、ｍ
ＧはＯ6 −メチルグアニンデオキシリボヌクレオチドを
示す。但し、各オリゴデオキシリボヌクレオチドの５’
末端と３’末端の水酸基は含まない。なお、各配列の左
末端が５’末端であり、右末端が３’末端である。さら
に、ｅ、ｆ又はｇがＡ、Ｇ、Ｃ又はＴの間に挿入されて
いる場合は、ホスホジエステル基がホスホロチオエート
型ジエステル基（ｅ）、メチルホスホネート型ジエステ
ル基（ｆ）あるいはメトキシエチルアミノホスフェート
型ジエステル基（ｇ）に変換されていることを示す。）4. A compound or a salt thereof according to claim 1, wherein B is an oligodeoxyribonucleotide selected from the following group A: [Group A] TGGGAeG, TGGGeAeG, TGGe
GeAeG, TGeGeGeAeG, TeGeGeGeGe
AeG, TGGeGAeG, TGGeGAG, TGGG
AfG, TGGGfAfG, TGGfGfAfG, TG
fGfGfAfG, TGGGAgG, TGGGgAg
G, TGGgGgAgG, TGgGgGgAgG, TG
GGeA, TGGGeG, TGGeGeG, TGGeG
G, TGGeG, TGGGAGeG, CGGGAGe
G, TTGGAGeG, TTGGGAGeG, TGCG
AGeG, GGGGAGeG, mCGGGAGfG, m
CGmCGAGgG, CTGGGAGeG, GGGCG
GGeC, TAGGAGeG, TGGGAGGeT, T
GGGGCGCAeG, CCeG, TCGGAGeG, T
GmCGAGeG, GTGGGAGeG, TGeG, T
GGGAmGeG, TGGGAGeA, AATGGGA
GeG, TTGGGeG, TTGGeGeG, TTGG
eGG, TGGGGeG, TGGGeGeG, TGGG
eGG, CGGGeG, CGGeGeG, CGGeG
G, CGCGeG, CGCeGeG, CGCeGG, C
GGGeT, TGGGeC, TGGGeT (A group, A
Is adenine deoxyribonucleotide, G is guanine deoxyribonucleotide, C is cytosine deoxyribonucleotide, T is thymine deoxyribonucleotide, m
C is 5-methylcytosine deoxyribonucleotide, m
G represents O 6 -methylguanine deoxyribonucleotide. However, 5'of each oligodeoxyribonucleotide
It does not include hydroxyl groups at the terminal and 3'end. The left end of each sequence is the 5'end and the right end is the 3'end. Further, when e, f or g is inserted between A, G, C or T, the phosphodiester group is a phosphorothioate type diester group (e), a methylphosphonate type diester group (f) or methoxyethylaminophosphate. It shows that it has been converted to a type diester group (g). )
されるオリゴデオキシリボヌクレオチドである化合物又
はその塩。 ［Ｂ群］ＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧｅ
ＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，ＴｅＧｅＧｅＧｅ
ＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧＧ
ＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆＡｆＧ，ＴＧ
ｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧＧＧｇＡｇ
Ｇ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧ
ＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧ
Ｇ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧＧＡＧｅ
Ｇ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，ＴＧＣＧ
ＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧｆＧ，ｍ
ＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，ＴＴＧＧＧ
ｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，ＴＧＧＧＧ
ｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，ＣＧＧＧｅ
Ｇ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，Ｃ
ＧＣｅＧｅＧ，ＣＧＣｅＧＧ（Ｂ群中、Ａはアデニンデ
オキシリボヌクレオチド、Ｇはグアニンデオキシリボヌ
クレオチド、Ｃはシトシンデオキシリボヌクレオチド、
Ｔはチミンデオキシリボヌクレオチド、ｍＣは５−メチ
ルシトシンデオキシリボヌクレオチドを示す。但し、各
オリゴデオキシリボヌクレオチドの５’末端と３’末端
の水酸基は含まない。なお、各配列の左末端が５’末端
であり、右末端が３’末端である。さらに、ｅ、ｆ又は
ｇがＡ、Ｇ、Ｃ又はＴの間に挿入されている場合は、ホ
スホジエステル基がホスホロチオエート型ジエステル基
（ｅ）、メチルホスホネート型ジエステル基（ｆ）ある
いはメトキシエチルアミノホスフェート型ジエステル基
（ｇ）に変換されていることを示す。）5. The compound according to claim 1, wherein B is an oligodeoxyribonucleotide selected from the following group B or a salt thereof. [Group B] TGGGAeG, TGGGeAeG, TGGe
GeAeG, TGeGeGeAeG, TeGeGeGeGe
AeG, TGGeGAeG, TGGeGAG, TGGG
AfG, TGGGfAfG, TGGfGfAfG, TG
fGfGfAfG, TGGGAgG, TGGGgAg
G, TGGgGgAgG, TGgGgGgAgG, TG
GGeA, TGGGeG, TGGeGeG, TGGeG
G, TGGeG, TGGGAGeG, CGGGAGe
G, TTGGAGeG, TTGGGAGeG, TGCG
AGeG, GGGGAGeG, mCGGGAGfG, m
CGmCGAGgG, CTGGGAGeG, TTGGG
eG, TTGGeGeG, TTGGeGG, TGGGGG
eG, TGGGeGeG, TGGGeGG, CGGGe
G, CGGeGeG, CGGeGG, CGCGeG, C
GCeGeG, CGCeGG (in group B, A is adenine deoxyribonucleotide, G is guanine deoxyribonucleotide, C is cytosine deoxyribonucleotide,
T represents thymine deoxyribonucleotide, and mC represents 5-methylcytosine deoxyribonucleotide. However, the hydroxyl groups at the 5'end and 3'end of each oligodeoxyribonucleotide are not included. The left end of each sequence is the 5'end and the right end is the 3'end. Further, when e, f or g is inserted between A, G, C or T, the phosphodiester group is a phosphorothioate type diester group (e), a methylphosphonate type diester group (f) or methoxyethylaminophosphate. It shows that it has been converted to a type diester group (g). )
1 及びＺの組み合わせにより得られる５’末端の基（Ｒ
1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、トリフェニルメチルオキシ、
３，４−（ジベンジルオキシ）ベンジルオキシ、３，５
−（ジベンジルオキシ）ベンジルオキシ、３，５−ビス
［３，５−（ジベンジルオキシ）ベンジルオキシ］ベン
ジルオキシ、ｔ−ブチルジフェニルシリルオキシ、フェ
ニルフルオレニルオキシ、フェニルキサンテニルオキシ
基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組
み合わせにより得られる３’末端の基（［Ｐ（Ｏ）（Ｙ
2 Ｒ4 ）−Ｙ3−（Ｘ−Ｙ4 ）n ］m Ｈ）が、水素、メ
チルホスホリル、２−クロロフェニルホスホリル、−Ｏ
−メチルチオホスホリル、メチルホスホニル、メチルチ
オホスホニル、フェニルホスホニル、２−ヒドロキシエ
チルホスホリル、−Ｏ−（２−ヒドロキシエチル）チオ
ホスホリル、フェニルホスホリル、４−クロロフェニル
ホスホリル、２−ニトロフェニルホスホリル、４−ニト
ロフェニルホスホリル、エチルホスホリル、−Ｏ−エチ
ルチオホスホリルであり、ＢがＴＧＧＧＡｅＧ，ＴＧＧ
ＧｅＡｅＧ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅ
Ｇ，ＴｅＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧ
ＧｅＧＡＧ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧ
ＧｆＧｆＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇ
Ｇ，ＴＧＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧ
ｇＧｇＡｇＧ，ＴＧＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅ
ＧｅＧ，ＴＧＧｅＧＧ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅ
Ｇ，ＣＧＧＧＡＧｅＧ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧ
ＡＧｅＧ，ＴＧＣＧＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣ
ＧＧＧＡＧｆＧ，ｍＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡ
ＧｅＧ，ＧＧＧＣＧＧＧｅＣ，ＴＡＧＧＡＧｅＧ，ＴＧ
ＧＧＡＧＧｅＴ，ＴＧＧＧＣＧＣＡｅＧ，ＣＣｅＧ，Ｔ
ＣＧＧＡＧｅＧ，ＴＧｍＣＧＡＧｅＧ，ＧＴＧＧＧＡＧ
ｅＧ，ＴＧｅＧ，ＴＧＧＧＡｍＧｅＧ，ＴＧＧＧＡＧｅ
Ａ，ＡＡＴＧＧＧＡＧｅＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧ
ｅＧｅＧ，ＴＴＧＧｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧ
ｅＧｅＧ，ＴＧＧＧｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧ
ｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ，
ＣＧＣｅＧＧ，ＣＧＧＧｅＴ，ＴＧＧＧｅＣ又はＴＧＧ
ＧｅＴである化合物。6. The method according to claim 1, wherein R 1 , R 2 , R 3 , Y
5 'end of the group obtained by the combination of 1 and Z (R
1 R 2 R 3 Z-Y 1 ) is triphenylmethyloxy,
3,4- (dibenzyloxy) benzyloxy, 3,5
-(Dibenzyloxy) benzyloxy, 3,5-bis [3,5- (dibenzyloxy) benzyloxy] benzyloxy, t-butyldiphenylsilyloxy, phenylfluorenyloxy and phenylxanthenyloxy groups. , R 4 , X, Y 2 , Y 3 , Y 4 , m and n are combined to obtain a 3'terminal group ([P (O) (Y
2 R 4) -Y 3 - ( X-Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-chlorophenyl phosphoryl, -O
-Methylthiophosphoryl, methylphosphonyl, methylthiophosphonyl, phenylphosphonyl, 2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl, phenylphosphoryl, 4-chlorophenylphosphoryl, 2-nitrophenylphosphoryl, 4- Nitrophenylphosphoryl, ethylphosphoryl, -O-ethylthiophosphoryl, B is TGGGAeG, TGG.
GeAeG, TGGeGeAeG, TGeGeGeAe
G, TeGeGeGeGeAeG, TGGeGAeG, TG
GeGAG, TGGGAfG, TGGGfAfG, TG
GfGfAfG, TGfGfGfAfG, TGGGAg
G, TGGGgAgG, TGGgGgAgG, TGgG
gGgAgG, TGGGeA, TGGGeG, TGGe
GeG, TGGeGG, TGGeG, TGGGAGe
G, CGGGAGeG, TTGGAGeG, TTGGG
AGeG, TGCGAGeG, GGGGAGeG, mC
GGGAGfG, mCGmCGAGgG, CTGGGA
GeG, GGGCGGGeC, TAGGAGeG, TG
GGAGGeT, TGGGCGCAeG, CCeG, T
CGGAGeG, TGmCGAGeG, GTGGGAG
eG, TGeG, TGGGAmGeG, TGGGAGe
A, AATGGGAGeG, TTGGGeG, TTGG
eGeG, TTGGeGG, TGGGGEg, TGGG
eGeG, TGGGeGG, CGGGeG, CGGeG
eG, CGGeGG, CGCGeG, CGCeGeG,
CGCeGG, CGGGeT, TGGGeC or TGG
A compound that is GeT.
1 及びＺの組み合わせにより得られる５’末端の基（Ｒ
1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、トリフェニルメチルオキシ、
３，４−（ジベンジルオキシ）ベンジルオキシ、３，５
−（ジベンジルオキシ）ベンジルオキシ、３，５−ビス
［３，５−（ジベンジルオキシ）ベンジルオキシ］ベン
ジルオキシ、ｔ−ブチルジフェニルシリルオキシ、フェ
ニルフルオレニルオキシ、フェニルキサンテニルオキシ
基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組
み合わせにより得られる３’末端の基（［Ｐ（Ｏ）（Ｙ
2 Ｒ4 ）−Ｙ3−（Ｘ−Ｙ4 ）n ］m Ｈ）が、水素、メ
チルホスホリル、２−クロロフェニルホスホリル、−Ｏ
−メチルチオホスホリル、メチルホスホニル、メチルチ
オホスホニル、フェニルホスホニル、２−ヒドロキシエ
チルホスホリル、−Ｏ−（２−ヒドロキシエチル）チオ
ホスホリル、フェニルホスホリル、４−クロロフェニル
ホスホリル、２−ニトロフェニルホスホリル、４−ニト
ロフェニルホスホリル、エチルホスホリル、−Ｏ−エチ
ルチオホスホリルであり、ＢがＴＧＧＧＡｅＧ，ＴＧＧ
ＧｅＡｅＧ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅ
Ｇ，ＴｅＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧ
ＧｅＧＡＧ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧ
ＧｆＧｆＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇ
Ｇ，ＴＧＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧ
ｇＧｇＡｇＧ，ＴＧＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅ
ＧｅＧ，ＴＧＧｅＧＧ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅ
Ｇ，ＣＧＧＧＡＧｅＧ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧ
ＡＧｅＧ，ＴＧＣＧＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣ
ＧＧＧＡＧｆＧ，ｍＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡ
ＧｅＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧ
ｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧ
ｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧ
Ｇ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ又はＣＧＣｅＧＧで
ある化合物。7. The method according to claim 1, wherein R 1 , R 2 , R 3 , Y
5 'end of the group obtained by the combination of 1 and Z (R
1 R 2 R 3 Z-Y 1 ) is triphenylmethyloxy,
3,4- (dibenzyloxy) benzyloxy, 3,5
-(Dibenzyloxy) benzyloxy, 3,5-bis [3,5- (dibenzyloxy) benzyloxy] benzyloxy, t-butyldiphenylsilyloxy, phenylfluorenyloxy and phenylxanthenyloxy groups. , R 4 , X, Y 2 , Y 3 , Y 4 , m and n are combined to obtain a 3'terminal group ([P (O) (Y
2 R 4) -Y 3 - ( X-Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-chlorophenyl phosphoryl, -O
-Methylthiophosphoryl, methylphosphonyl, methylthiophosphonyl, phenylphosphonyl, 2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl, phenylphosphoryl, 4-chlorophenylphosphoryl, 2-nitrophenylphosphoryl, 4- Nitrophenylphosphoryl, ethylphosphoryl, -O-ethylthiophosphoryl, B is TGGGAeG, TGG.
GeAeG, TGGeGeAeG, TGeGeGeAe
G, TeGeGeGeGeAeG, TGGeGAeG, TG
GeGAG, TGGGAfG, TGGGfAfG, TG
GfGfAfG, TGfGfGfAfG, TGGGAg
G, TGGGgAgG, TGGgGgAgG, TGgG
gGgAgG, TGGGeA, TGGGeG, TGGe
GeG, TGGeGG, TGGeG, TGGGAGe
G, CGGGAGeG, TTGGAGeG, TTGGG
AGeG, TGCGAGeG, GGGGAGeG, mC
GGGAGfG, mCGmCGAGgG, CTGGGA
GeG, TTGGGeG, TTGGeGeG, TTGG
eGG, TGGGGeG, TGGGeGeG, TGGG
eGG, CGGGeG, CGGeGeG, CGGeG
A compound which is G, CGCGeG, CGCeGeG or CGCeGG.
1 及びＺの組み合わせにより得られる５’末端の基（Ｒ
1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、トリフェニルメチルオキシ、
３，４−（ジベンジルオキシ）ベンジルオキシ、３，５
−（ジベンジルオキシ）ベンジルオキシ、３，５−ビス
［３，５−（ジベンジルオキシ）ベンジルオキシ］ベン
ジルオキシ、ｔ−ブチルジフェニルシリルオキシ、フェ
ニルフルオレニルオキシ、フェニルキサンテニルオキシ
基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組
み合わせにより得られる３’末端の基（［Ｐ（Ｏ）（Ｙ
2 Ｒ4 ）−Ｙ3−（Ｘ−Ｙ4 ）n ］m Ｈ）が、水素、メ
チルホスホリル、２−クロロフェニルホスホリル、−Ｏ
−メチルチオホスホリル、メチルホスホニル、メチルチ
オホスホニル、フェニルホスホニル、２−ヒドロキシエ
チルホスホリル、−Ｏ−（２−ヒドロキシエチル）チオ
ホスホリル基であり、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧｅ
ＡｅＧ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，
ＴｅＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅ
ＧＡＧ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆ
ＧｆＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，
ＴＧＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧ
ｇＡｇＧ，ＴＧＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅ
Ｇ，ＴＧＧｅＧＧ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，Ｃ
ＧＧＧＡＧｅＧ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅ
Ｇ，ＴＧＣＧＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧ
ＡＧｆＧ，ｍＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅ
Ｇ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧ
Ｇ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧ
Ｇ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，Ｃ
ＧＣＧｅＧ，ＣＧＣｅＧｅＧ又はＣＧＣｅＧＧである化
合物。8. The method according to claim 1, wherein R 1 , R 2 , R 3 , Y
5 'end of the group obtained by the combination of 1 and Z (R
1 R 2 R 3 Z-Y 1 ) is triphenylmethyloxy,
3,4- (dibenzyloxy) benzyloxy, 3,5
-(Dibenzyloxy) benzyloxy, 3,5-bis [3,5- (dibenzyloxy) benzyloxy] benzyloxy, t-butyldiphenylsilyloxy, phenylfluorenyloxy and phenylxanthenyloxy groups. , R 4 , X, Y 2 , Y 3 , Y 4 , m and n are combined to obtain a 3'terminal group ([P (O) (Y
2 R 4) -Y 3 - ( X-Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-chlorophenyl phosphoryl, -O
-Methylthiophosphoryl, methylphosphonyl, methylthiophosphonyl, phenylphosphonyl, 2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl group, B is TGGGAeG, TGGGe.
AeG, TGGeGeAeG, TGeGeGeAeG,
TeGeGeGeGeAeG, TGGeGAeG, TGGe
GAG, TGGGAfG, TGGGfAfG, TGGf
GfAfG, TGfGfGfAfG, TGGGAgG,
TGGGgAgG, TGGgGgAgG, TGgGgG
gAgG, TGGGeA, TGGGeG, TGGeGe
G, TGGeGG, TGGeG, TGGGAGeG, C
GGGAGeG, TTGGAGeG, TTGGGAGe
G, TGCGAGeG, GGGGAGeG, mCGGG
AGfG, mCGmCGAGgG, CTGGGAGe
G, TTGGGeG, TTGGeGeG, TTGGeG
G, TGGGGeG, TGGGeGeG, TGGGGeG
G, CGGGeG, CGGeGeG, CGGeGG, C
A compound which is GCGeG, CGCeGeG or CGCeGG.
1 及びＺの組み合わせにより得られる５’末端の基（Ｒ
1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、トリフェニルメチルオキシ、
３，４−（ジベンジルオキシ）ベンジルオキシ、３，５
−（ジベンジルオキシ）ベンジルオキシ基であり、Ｒ
4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組み合わせによ
り得られる３’末端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ
3 −（Ｘ−Ｙ4 ）n ］mＨ）が、水素、メチルホスホリ
ル、２−クロロフェニルホスホリル、−Ｏ−メチルチオ
ホスホリル、メチルホスホニル、メチルチオホスホニ
ル、フェニルホスホニル、２−ヒドロキシエチルホスホ
リル、−Ｏ−（２−ヒドロキシエチル）チオホスホリ
ル、フェニルホスホリル、４−クロロフェニルホスホリ
ル、２−ニトロフェニルホスホリル、４−ニトロフェニ
ルホスホリル、エチルホスホリル、−Ｏ−エチルチオホ
スホリルであり、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅ
Ｇ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，Ｔｅ
ＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡ
Ｇ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆ
ＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧ
ＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡ
ｇＧ，ＴＧＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，
ＴＧＧｅＧＧ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧ
ＧＡＧｅＧ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，
ＴＧＣＧＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧ
ｆＧ，ｍＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，Ｔ
ＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，Ｔ
ＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，Ｃ
ＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧ
ｅＧ，ＣＧＣｅＧｅＧ又はＣＧＣｅＧＧである化合物。9. The method according to claim 1, wherein R 1 , R 2 , R 3 , Y
5 'end of the group obtained by the combination of 1 and Z (R
1 R 2 R 3 Z-Y 1 ) is triphenylmethyloxy,
3,4- (dibenzyloxy) benzyloxy, 3,5
A-(dibenzyloxy) benzyloxy group, R
4, X, Y 2, Y 3, Y 4, are obtained by a combination of m and n 3 'end of the group ([P (O) (Y 2 R 4) -Y
3 - (X-Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-chlorophenyl phosphoryl, -O- methyl thio phosphoryl, Mechiruhosuhoniru, methyl thio phosphonyl, phenyl phosphonyl, 2-hydroxyethyl phosphoryl, - O- (2-hydroxyethyl) thiophosphoryl, phenylphosphoryl, 4-chlorophenylphosphoryl, 2-nitrophenylphosphoryl, 4-nitrophenylphosphoryl, ethylphosphoryl, -O-ethylthiophosphoryl, and B is TGGGAeG, TGGGeAe.
G, TGGeGeAeG, TGeGeGeAeG, Te
GeGeGeAeG, TGGeGAeG, TGGeGA
G, TGGGAfG, TGGGfAfG, TGGfGf
AfG, TGfGfGfAfG, TGGGAgG, TG
GGgAgG, TGGgGgAgG, TGgGgGgA
gG, TGGGeA, TGGGeG, TGGeGeG,
TGGeGG, TGGeG, TGGGAGeG, CGG
GAGeG, TTGGAGeG, TTGGGAGeG,
TGCGAGeG, GGGGAGeG, mCGGGAG
fG, mCGmCGAGgG, CTGGGAGeG, T
TGGGeG, TTGGeGeG, TTGGeGG, T
GGGGeG, TGGGeGeG, TGGGeGG, C
GGGeG, CGGeGeG, CGGeGG, CGCG
A compound that is eG, CGCeGeG or CGCeGG.
Ｙ1 及びＺの組み合わせにより得られる５’末端の基
（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、トリフェニルメチルオキ
シ、３，４−（ジベンジルオキシ）ベンジルオキシ、
３，５−（ジベンジルオキシ）ベンジルオキシ基であ
り、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの組み合わ
せにより得られる３’末端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ
4 ）−Ｙ3 −（Ｘ−Ｙ4 ）n ］mＨ）が水素、メチルホ
スホリル、２−クロロフェニルホスホリル、−Ｏ−メチ
ルチオホスホリル、メチルホスホニル、メチルチオホス
ホニル、フェニルホスホニル、２−ヒドロキシエチルホ
スホリル、−Ｏ−（２−ヒドロキシエチル）チオホスホ
リル基であり、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅ
Ｇ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，Ｔｅ
ＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡ
Ｇ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆ
ＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧ
ＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡ
ｇＧ，ＴＧＧＧｅＡ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，
ＴＧＧｅＧＧ，ＴＧＧｅＧ，ＴＧＧＧＡＧｅＧ，ＣＧＧ
ＧＡＧｅＧ，ＴＴＧＧＡＧｅＧ，ＴＴＧＧＧＡＧｅＧ，
ＴＧＣＧＡＧｅＧ，ＧＧＧＧＡＧｅＧ，ｍＣＧＧＧＡＧ
ｆＧ，ｍＣＧｍＣＧＡＧｇＧ，ＣＴＧＧＧＡＧｅＧ，Ｔ
ＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，Ｔ
ＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，Ｃ
ＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧ
ｅＧ，ＣＧＣｅＧｅＧ又はＧＣｅＧＧである化合物。10. The method according to claim 1, wherein R 1 , R 2 , R 3 and
The 5'-terminal group (R 1 R 2 R 3 Z-Y 1 ) obtained by the combination of Y 1 and Z is triphenylmethyloxy, 3,4- (dibenzyloxy) benzyloxy,
3,5- (dibenzyloxy) benzyloxy group, which is a 3'-terminal group ([P (O) (Y) obtained by combining R 4 , X, Y 2 , Y 3 , Y 4 , m and n. 2 R
4) -Y 3 - (X- Y 4) n] m H) is hydrogen, Mechiruhosuhoriru, 2-chlorophenyl phosphoryl, -O- methyl thio phosphoryl, Mechiruhosuhoniru, methyl thio phosphonyl, phenyl phosphonyl, 2-hydroxyethyl Phosphoryl, -O- (2-hydroxyethyl) thiophosphoryl group, B is TGGGAeG, TGGGeAe.
G, TGGeGeAeG, TGeGeGeAeG, Te
GeGeGeAeG, TGGeGAeG, TGGeGA
G, TGGGAfG, TGGGfAfG, TGGfGf
AfG, TGfGfGfAfG, TGGGAgG, TG
GGgAgG, TGGgGgAgG, TGgGgGgA
gG, TGGGeA, TGGGeG, TGGeGeG,
TGGeGG, TGGeG, TGGGAGeG, CGG
GAGeG, TTGGAGeG, TTGGGAGeG,
TGCGAGeG, GGGGAGeG, mCGGGAG
fG, mCGmCGAGgG, CTGGGAGeG, T
TGGGeG, TTGGeGeG, TTGGeGG, T
GGGGeG, TGGGeGeG, TGGGeGG, C
GGGeG, CGGeGeG, CGGeGG, CGCG
A compound that is eG, CGCeGeG or GCeGG.
Ｙ1 及びＺの組み合わせにより得られる５’末端の基
（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、トリフェニルメチルオキ
シ基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ3 、Ｙ4 、ｍ及びｎの
組み合わせにより得られる３’末端の基（［Ｐ（Ｏ）
（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−Ｙ4 ）n ］m Ｈ）が水素、
メチルホスホリル、２−ヒドロキシエチルホスホリル、
−Ｏ−（２−ヒドロキシエチル）チオホスホリル基であ
り、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧｅＡｅＧ，ＴＧＧｅ
ＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅＧ，ＴｅＧｅＧｅＧｅ
ＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧＧ
ＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧＧｆＧｆＡｆＧ，ＴＧ
ｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇＧ，ＴＧＧＧｇＡｇ
Ｇ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧｇＧｇＡｇＧ，ＴＧ
ＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧｅＧＧ，ＴＴＧＧＧ
ｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧｅＧＧ，ＴＧＧＧＧ
ｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧｅＧＧ，ＣＧＧＧｅ
Ｇ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，Ｃ
ＧＣｅＧｅＧ又はＣＧＣｅＧＧである化合物。11. The method according to claim 1, wherein R 1 , R 2 , R 3 and
The 5′-terminal group (R 1 R 2 R 3 Z—Y 1 ) obtained by the combination of Y 1 and Z is a triphenylmethyloxy group, and R 4 , X, Y 2 , Y 3 , Y 4 , A group at the 3'end obtained by the combination of m and n ([P (O)
(Y 2 R 4) -Y 3 - (X-Y 4) n] m H) is hydrogen,
Methylphosphoryl, 2-hydroxyethylphosphoryl,
Is an -O- (2-hydroxyethyl) thiophosphoryl group, and B is TGGGAeG, TGGGeAeG, TGGe.
GeAeG, TGeGeGeAeG, TeGeGeGeGe
AeG, TGGeGAeG, TGGeGAG, TGGG
AfG, TGGGfAfG, TGGfGfAfG, TG
fGfGfAfG, TGGGAgG, TGGGgAg
G, TGGgGgAgG, TGgGgGgAgG, TG
GGeG, TGGeGeG, TGGeGG, TTGGGG
eG, TTGGeGeG, TTGGeGG, TGGGGG
eG, TGGGeGeG, TGGGeGG, CGGGe
G, CGGeGeG, CGGeGG, CGCGeG, C
A compound that is GCeGeG or CGCeGG.
Ｙ1 及びＺの組み合わせにより得られる５’末端の基
（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、３，４−（ジベンジルオ
キシ）ベンジルオキシ、基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ
3 、Ｙ4 、ｍ及びｎの組み合わせにより得られる３’末
端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−Ｙ4 ）
n］m Ｈ）が水素、メチルホスホリル、２−ヒドロキシ
エチルホスホリル、−Ｏ−（２−ヒドロキシエチル）チ
オホスホリル基であり、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧ
ｅＡｅＧ，ＴＧＧｅＧｅＡｅＧ，ＴＧｅＧｅＧｅＡｅ
Ｇ，ＴｅＧｅＧｅＧｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧ
ＧｅＧＡＧ，ＴＧＧＧＡｆＧ，ＴＧＧＧｆＡｆＧ，ＴＧ
ＧｆＧｆＡｆＧ，ＴＧｆＧｆＧｆＡｆＧ，ＴＧＧＧＡｇ
Ｇ，ＴＧＧＧｇＡｇＧ，ＴＧＧｇＧｇＡｇＧ，ＴＧｇＧ
ｇＧｇＡｇＧ，ＴＧＧＧｅＧ，ＴＧＧｅＧｅＧ，ＴＧＧ
ｅＧＧ，ＴＴＧＧＧｅＧ，ＴＴＧＧｅＧｅＧ，ＴＴＧＧ
ｅＧＧ，ＴＧＧＧＧｅＧ，ＴＧＧＧｅＧｅＧ，ＴＧＧＧ
ｅＧＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧｅＧ，ＣＧＧｅＧ
Ｇ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ又はＣＧＣｅＧＧで
ある化合物。12. The method according to claim 1, wherein R 1 , R 2 , R 3 and
The 5′-terminal group (R 1 R 2 R 3 Z—Y 1 ) obtained by the combination of Y 1 and Z is 3,4- (dibenzyloxy) benzyloxy, a group, and R 4 , X, Y 2 , Y
3, Y 4, 3 is obtained by a combination of m and n 'terminus of groups ([P (O) (Y 2 R 4) -Y 3 - (X-Y 4)
n ] m H) is hydrogen, methylphosphoryl, 2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl group, and B is TGGGAeG, TGGG.
eAeG, TGGeGeAeG, TGeGeGeAe
G, TeGeGeGeGeAeG, TGGeGAeG, TG
GeGAG, TGGGAfG, TGGGfAfG, TG
GfGfAfG, TGfGfGfAfG, TGGGAg
G, TGGGgAgG, TGGgGgAgG, TGgG
gGgAgG, TGGGeG, TGGeGeG, TGG
eGG, TTGGGeG, TTGGeGeG, TTGG
eGG, TGGGGeG, TGGGeGeG, TGGG
eGG, CGGGeG, CGGeGeG, CGGeG
A compound which is G, CGCGeG, CGCeGeG or CGCeGG.
Ｙ1 及びＺの組み合わせにより得られる５’末端の基
（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、３，４−（ジベンジルオ
キシ）ベンジルオキシ、基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ
3 、Ｙ4 、ｍ及びｎの組み合わせにより得られる３’末
端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−Ｙ4 ）
n］m Ｈ）が水素、メチルホスホリル、２−ヒドロキシ
エチルホスホリル、−Ｏ−（２−ヒドロキシエチル）チ
オホスホリル基であり、ＢがＴＧＧＧＡｅＧ，ＴＧＧＧ
ｅＡｅＧ，ＴＧＧｅＧＡｅＧ，ＴＧＧｅＧＡＧ，ＴＧＧ
ＧＡｆＧ，ＴＧＧＧＡｇＧ，ＣＧＧＧｅＧ，ＣＧＧｅＧ
ｅＧ，ＣＧＧｅＧＧ，ＣＧＣＧｅＧ，ＣＧＣｅＧｅＧ又
はＣＧＣｅＧＧである化合物。13. The method according to claim 1, wherein R 1 , R 2 , R 3 and
The 5′-terminal group (R 1 R 2 R 3 Z—Y 1 ) obtained by the combination of Y 1 and Z is 3,4- (dibenzyloxy) benzyloxy, a group, and R 4 , X, Y 2 , Y
3, Y 4, 3 is obtained by a combination of m and n 'terminus of groups ([P (O) (Y 2 R 4) -Y 3 - (X-Y 4)
n ] m H) is hydrogen, methylphosphoryl, 2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl group, and B is TGGGAeG, TGGG.
eAeG, TGGeGAeG, TGGeGAG, TGG
GAfG, TGGGAgG, CGGGeG, CGGeG
A compound that is eG, CGGeGG, CGCGeG, CGCeGeG or CGCeGG.
Ｙ1 及びＺの組み合わせにより得られる５’末端の基
（Ｒ1 Ｒ2 Ｒ3 Ｚ−Ｙ1 ）が、３，４−（ジベンジルオ
キシ）ベンジルオキシ、基であり、Ｒ4 、Ｘ、Ｙ2 、Ｙ
3 、Ｙ4 、ｍ及びｎの組み合わせにより得られる３’末
端の基（［Ｐ（Ｏ）（Ｙ2 Ｒ4 ）−Ｙ3 −（Ｘ−Ｙ4 ）
n］m Ｈ）が水素、メチルホスホリル、２−ヒドロキシ
エチルホスホリル、−Ｏ−（２−ヒドロキシエチル）チ
オホスホリル基であり、ＢがＴＧＧＧＡｅＧ，ＣＧＧＧ
ｅＧ又はＣＧＣＧｅＧである化合物。14. The method according to claim 1, wherein R 1 , R 2 , R 3 and
The 5′-terminal group (R 1 R 2 R 3 Z—Y 1 ) obtained by the combination of Y 1 and Z is 3,4- (dibenzyloxy) benzyloxy, a group, and R 4 , X, Y 2 , Y
3, Y 4, 3 is obtained by a combination of m and n 'terminus of groups ([P (O) (Y 2 R 4) -Y 3 - (X-Y 4)
n ] m H) is hydrogen, methylphosphoryl, 2-hydroxyethylphosphoryl, -O- (2-hydroxyethyl) thiophosphoryl group, and B is TGGGAeG, CGGG.
A compound that is eG or CGCGeG.
る抗エイズ剤。15. An anti-AIDS agent comprising the compound according to claim 1 as an active ingredient.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP7185115A JPH0892275A (en) | 1994-07-25 | 1995-07-21 | Modified oligodeoxyribonucleotide |
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP17232594 | 1994-07-25 | ||
| JP6-172325 | 1994-07-25 | ||
| JP7185115A JPH0892275A (en) | 1994-07-25 | 1995-07-21 | Modified oligodeoxyribonucleotide |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPH0892275A true JPH0892275A (en) | 1996-04-09 |
Family
ID=26494719
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP7185115A Pending JPH0892275A (en) | 1994-07-25 | 1995-07-21 | Modified oligodeoxyribonucleotide |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0892275A (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005116207A1 (en) * | 2004-05-28 | 2005-12-08 | Sankyo Company, Limited | Telomerase-inhibitory ena oligonucleotide |
| JPWO2022172994A1 (en) * | 2021-02-12 | 2022-08-18 |
-
1995
- 1995-07-21 JP JP7185115A patent/JPH0892275A/en active Pending
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2005116207A1 (en) * | 2004-05-28 | 2005-12-08 | Sankyo Company, Limited | Telomerase-inhibitory ena oligonucleotide |
| JPWO2022172994A1 (en) * | 2021-02-12 | 2022-08-18 | ||
| WO2022172994A1 (en) * | 2021-02-12 | 2022-08-18 | 味の素株式会社 | Oligonucleotide production method |
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