WO2006088256A1 - 1,2−トランスグリコシド化合物の製造方法 - Google Patents
1,2−トランスグリコシド化合物の製造方法 Download PDFInfo
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- WO2006088256A1 WO2006088256A1 PCT/JP2006/303519 JP2006303519W WO2006088256A1 WO 2006088256 A1 WO2006088256 A1 WO 2006088256A1 JP 2006303519 W JP2006303519 W JP 2006303519W WO 2006088256 A1 WO2006088256 A1 WO 2006088256A1
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- 238000000034 method Methods 0.000 title claims abstract description 13
- -1 glycoside compound Chemical class 0.000 claims abstract description 107
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 39
- 125000001424 substituent group Chemical group 0.000 claims abstract description 33
- 229930182470 glycoside Natural products 0.000 claims abstract description 13
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 11
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims abstract description 5
- 150000001875 compounds Chemical class 0.000 claims description 81
- 125000004432 carbon atom Chemical group C* 0.000 claims description 36
- 125000000217 alkyl group Chemical group 0.000 claims description 22
- 238000004519 manufacturing process Methods 0.000 claims description 19
- 125000006239 protecting group Chemical group 0.000 claims description 17
- 125000005843 halogen group Chemical group 0.000 claims description 15
- 125000003118 aryl group Chemical group 0.000 claims description 13
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 10
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 6
- WQZGKKKJIJFFOK-QTVWNMPRSA-N D-mannopyranose Chemical compound OC[C@H]1OC(O)[C@@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-QTVWNMPRSA-N 0.000 claims description 5
- WQZGKKKJIJFFOK-PHYPRBDBSA-N alpha-D-galactose Chemical compound OC[C@H]1O[C@H](O)[C@H](O)[C@@H](O)[C@H]1O WQZGKKKJIJFFOK-PHYPRBDBSA-N 0.000 claims description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 5
- 229960003082 galactose Drugs 0.000 claims description 5
- 150000004676 glycans Chemical class 0.000 claims description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims description 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 5
- 229920001282 polysaccharide Polymers 0.000 claims description 5
- 239000005017 polysaccharide Substances 0.000 claims description 5
- HMFHBZSHGGEWLO-SOOFDHNKSA-N D-ribofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@@H]1O HMFHBZSHGGEWLO-SOOFDHNKSA-N 0.000 claims description 4
- HMFHBZSHGGEWLO-IOVATXLUSA-N D-xylofuranose Chemical compound OC[C@H]1OC(O)[C@H](O)[C@H]1O HMFHBZSHGGEWLO-IOVATXLUSA-N 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- FMAORJIQYMIRHF-HERZVMAMSA-N (3R,4R)-Oxolane-2,3,4-triol Chemical compound O[C@@H]1COC(O)[C@@H]1O FMAORJIQYMIRHF-HERZVMAMSA-N 0.000 claims description 3
- 125000003277 amino group Chemical group 0.000 claims description 3
- 150000002243 furanoses Chemical class 0.000 claims description 3
- FMAORJIQYMIRHF-BCDHYOAOSA-N (3S,4R)-Oxolane-2,3,4-triol Chemical compound O[C@@H]1COC(O)[C@H]1O FMAORJIQYMIRHF-BCDHYOAOSA-N 0.000 claims description 2
- WVDDGKGOMKODPV-UHFFFAOYSA-N Benzyl alcohol Chemical compound OCC1=CC=CC=C1 WVDDGKGOMKODPV-UHFFFAOYSA-N 0.000 claims description 2
- 125000002723 alicyclic group Chemical group 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 150000003215 pyranoses Chemical class 0.000 claims description 2
- 230000007774 longterm Effects 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 2
- 125000003107 substituted aryl group Chemical group 0.000 abstract 1
- 239000013256 coordination polymer Substances 0.000 description 34
- 238000006243 chemical reaction Methods 0.000 description 24
- 239000000843 powder Substances 0.000 description 23
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- 229910019142 PO4 Inorganic materials 0.000 description 10
- 239000010452 phosphate Substances 0.000 description 10
- 239000002904 solvent Substances 0.000 description 10
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 8
- 239000002585 base Substances 0.000 description 8
- 239000012044 organic layer Substances 0.000 description 8
- HVHZEKKZMFRULH-UHFFFAOYSA-N 2,6-ditert-butyl-4-methylpyridine Chemical compound CC1=CC(C(C)(C)C)=NC(C(C)(C)C)=C1 HVHZEKKZMFRULH-UHFFFAOYSA-N 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910000104 sodium hydride Inorganic materials 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 4
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 4
- 235000019341 magnesium sulphate Nutrition 0.000 description 4
- 150000003214 pyranose derivatives Chemical class 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 101150117066 Lenep gene Proteins 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 230000003213 activating effect Effects 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 210000004027 cell Anatomy 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000012046 mixed solvent Substances 0.000 description 3
- 239000002808 molecular sieve Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 150000002905 orthoesters Chemical class 0.000 description 3
- 230000035484 reaction time Effects 0.000 description 3
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 3
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 3
- 235000017557 sodium bicarbonate Nutrition 0.000 description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 3
- 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 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- SRBFZHDQGSBBOR-IOVATXLUSA-N D-xylopyranose Chemical compound O[C@@H]1COC(O)[C@H](O)[C@H]1O SRBFZHDQGSBBOR-IOVATXLUSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- XPDWGBQVDMORPB-UHFFFAOYSA-N Fluoroform Chemical compound FC(F)F XPDWGBQVDMORPB-UHFFFAOYSA-N 0.000 description 2
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 2
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- SRBFZHDQGSBBOR-UHFFFAOYSA-N beta-D-Pyranose-Lyxose Natural products OC1COC(O)C(O)C1O SRBFZHDQGSBBOR-UHFFFAOYSA-N 0.000 description 2
- 239000006227 byproduct Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- XCIXKGXIYUWCLL-UHFFFAOYSA-N cyclopentanol Chemical compound OC1CCCC1 XCIXKGXIYUWCLL-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical group 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000706 filtrate Substances 0.000 description 2
- 238000003818 flash chromatography Methods 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 229930182830 galactose Natural products 0.000 description 2
- 239000008103 glucose Substances 0.000 description 2
- 238000006206 glycosylation reaction Methods 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000010410 layer Substances 0.000 description 2
- ZCSHNCUQKCANBX-UHFFFAOYSA-N lithium diisopropylamide Chemical compound [Li+].CC(C)[N-]C(C)C ZCSHNCUQKCANBX-UHFFFAOYSA-N 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 150000002772 monosaccharides Chemical class 0.000 description 2
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000012312 sodium hydride Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000003786 synthesis reaction Methods 0.000 description 2
- 125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- HDTRYLNUVZCQOY-UHFFFAOYSA-N α-D-glucopyranosyl-α-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OC1C(O)C(O)C(O)C(CO)O1 HDTRYLNUVZCQOY-UHFFFAOYSA-N 0.000 description 1
- KFEUJDWYNGMDBV-UHFFFAOYSA-N (N-Acetyl)-glucosamin-4-beta-galaktosid Natural products OC1C(NC(=O)C)C(O)OC(CO)C1OC1C(O)C(O)C(O)C(CO)O1 KFEUJDWYNGMDBV-UHFFFAOYSA-N 0.000 description 1
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- OQCFWECOQNPQCG-UHFFFAOYSA-N 1,3,4,8-tetrahydropyrimido[4,5-c]oxazin-7-one Chemical compound C1CONC2=C1C=NC(=O)N2 OQCFWECOQNPQCG-UHFFFAOYSA-N 0.000 description 1
- CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
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- FJLUATLTXUNBOT-UHFFFAOYSA-N 1-Hexadecylamine Chemical compound CCCCCCCCCCCCCCCCN FJLUATLTXUNBOT-UHFFFAOYSA-N 0.000 description 1
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- OWEGMIWEEQEYGQ-UHFFFAOYSA-N 100676-05-9 Natural products OC1C(O)C(O)C(CO)OC1OCC1C(O)C(O)C(O)C(OC2C(OC(O)C(O)C2O)CO)O1 OWEGMIWEEQEYGQ-UHFFFAOYSA-N 0.000 description 1
- YQTCQNIPQMJNTI-UHFFFAOYSA-N 2,2-dimethylpropan-1-one Chemical group CC(C)(C)[C]=O YQTCQNIPQMJNTI-UHFFFAOYSA-N 0.000 description 1
- MSWZFWKMSRAUBD-GASJEMHNSA-N 2-amino-2-deoxy-D-galactopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@H](O)[C@@H]1O MSWZFWKMSRAUBD-GASJEMHNSA-N 0.000 description 1
- MSWZFWKMSRAUBD-IVMDWMLBSA-N 2-amino-2-deoxy-D-glucopyranose Chemical compound N[C@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O MSWZFWKMSRAUBD-IVMDWMLBSA-N 0.000 description 1
- QTWJRLJHJPIABL-UHFFFAOYSA-N 2-methylphenol;3-methylphenol;4-methylphenol Chemical compound CC1=CC=C(O)C=C1.CC1=CC=CC(O)=C1.CC1=CC=CC=C1O QTWJRLJHJPIABL-UHFFFAOYSA-N 0.000 description 1
- IMOYOUMVYICGCA-UHFFFAOYSA-N 2-tert-butyl-4-hydroxyanisole Chemical compound COC1=CC=C(O)C=C1C(C)(C)C IMOYOUMVYICGCA-UHFFFAOYSA-N 0.000 description 1
- 229960000549 4-dimethylaminophenol Drugs 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- RZVAJINKPMORJF-UHFFFAOYSA-N Acetaminophen Chemical compound CC(=O)NC1=CC=C(O)C=C1 RZVAJINKPMORJF-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-XLOQQCSPSA-N Alpha-Lactose Chemical compound O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)O[C@H](O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-XLOQQCSPSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-CUHNMECISA-N D-Cellobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-CUHNMECISA-N 0.000 description 1
- RFSUNEUAIZKAJO-VRPWFDPXSA-N D-fructofuranose Chemical compound OC[C@H]1OC(O)(CO)[C@@H](O)[C@@H]1O RFSUNEUAIZKAJO-VRPWFDPXSA-N 0.000 description 1
- ZAFNJMIOTHYJRJ-UHFFFAOYSA-N Diisopropyl ether Chemical group CC(C)OC(C)C ZAFNJMIOTHYJRJ-UHFFFAOYSA-N 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- GUBGYTABKSRVRQ-QKKXKWKRSA-N Lactose Natural products OC[C@H]1O[C@@H](O[C@H]2[C@H](O)[C@@H](O)C(O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@H]1O GUBGYTABKSRVRQ-QKKXKWKRSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- GUBGYTABKSRVRQ-PICCSMPSSA-N Maltose Natural products O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@@H](CO)OC(O)[C@H](O)[C@H]1O GUBGYTABKSRVRQ-PICCSMPSSA-N 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- OVRNDRQMDRJTHS-ZTVVOAFPSA-N N-acetyl-D-mannosamine Chemical compound CC(=O)N[C@@H]1C(O)O[C@H](CO)[C@@H](O)[C@@H]1O OVRNDRQMDRJTHS-ZTVVOAFPSA-N 0.000 description 1
- KFEUJDWYNGMDBV-LODBTCKLSA-N N-acetyllactosamine Chemical compound O[C@@H]1[C@@H](NC(=O)C)[C@H](O)O[C@H](CO)[C@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KFEUJDWYNGMDBV-LODBTCKLSA-N 0.000 description 1
- HESSGHHCXGBPAJ-UHFFFAOYSA-N N-acetyllactosamine Natural products CC(=O)NC(C=O)C(O)C(C(O)CO)OC1OC(CO)C(O)C(O)C1O HESSGHHCXGBPAJ-UHFFFAOYSA-N 0.000 description 1
- 108091005461 Nucleic proteins Proteins 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930182473 O-glycoside Natural products 0.000 description 1
- 150000008444 O-glycosides Chemical class 0.000 description 1
- AYRXSINWFIIFAE-UHFFFAOYSA-N O6-alpha-D-Galactopyranosyl-D-galactose Natural products OCC1OC(OCC(O)C(O)C(O)C(O)C=O)C(O)C(O)C1O AYRXSINWFIIFAE-UHFFFAOYSA-N 0.000 description 1
- 229930182475 S-glycoside Natural products 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 101150052863 THY1 gene Proteins 0.000 description 1
- HDTRYLNUVZCQOY-WSWWMNSNSA-N Trehalose Natural products O[C@@H]1[C@@H](O)[C@@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-WSWWMNSNSA-N 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- KOOADCGQJDGAGA-UHFFFAOYSA-N [amino(dimethyl)silyl]methane Chemical compound C[Si](C)(C)N KOOADCGQJDGAGA-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 229910000288 alkali metal carbonate Inorganic materials 0.000 description 1
- 150000008041 alkali metal carbonates Chemical class 0.000 description 1
- 229910000102 alkali metal hydride Inorganic materials 0.000 description 1
- 150000008046 alkali metal hydrides Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- HDTRYLNUVZCQOY-LIZSDCNHSA-N alpha,alpha-trehalose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@@H]1O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 HDTRYLNUVZCQOY-LIZSDCNHSA-N 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 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
- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 description 1
- GUBGYTABKSRVRQ-QUYVBRFLSA-N beta-maltose Chemical compound OC[C@H]1O[C@H](O[C@H]2[C@H](O)[C@@H](O)[C@H](O)O[C@@H]2CO)[C@H](O)[C@@H](O)[C@@H]1O GUBGYTABKSRVRQ-QUYVBRFLSA-N 0.000 description 1
- 239000012472 biological sample Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N carbon tetrachloride Substances ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229930003836 cresol Natural products 0.000 description 1
- 125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000012024 dehydrating agents Substances 0.000 description 1
- 229940117389 dichlorobenzene Drugs 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 1
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- FKNQCJSGGFJEIZ-UHFFFAOYSA-N gamma-methylpyridine Natural products CC1=CC=NC=C1 FKNQCJSGGFJEIZ-UHFFFAOYSA-N 0.000 description 1
- DLRVVLDZNNYCBX-CQUJWQHSSA-N gentiobiose Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC[C@@H]1[C@@H](O)[C@H](O)[C@@H](O)C(O)O1 DLRVVLDZNNYCBX-CQUJWQHSSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 239000008241 heterogeneous mixture Substances 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 238000001727 in vivo Methods 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 125000002510 isobutoxy group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])O* 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000006317 isomerization reaction Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- SBUJHOSQTJFQJX-NOAMYHISSA-N kanamycin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N SBUJHOSQTJFQJX-NOAMYHISSA-N 0.000 description 1
- 229930027917 kanamycin Natural products 0.000 description 1
- 229960000318 kanamycin Drugs 0.000 description 1
- 229930182823 kanamycin A Natural products 0.000 description 1
- PVTHJAPFENJVNC-MHRBZPPQSA-N kasugamycin Chemical compound N[C@H]1C[C@H](NC(=N)C(O)=O)[C@@H](C)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@H](O)[C@@H]1O PVTHJAPFENJVNC-MHRBZPPQSA-N 0.000 description 1
- 239000008101 lactose Substances 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 229910003002 lithium salt Inorganic materials 0.000 description 1
- 159000000002 lithium salts Chemical class 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 125000006606 n-butoxy group Chemical group 0.000 description 1
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 108020004707 nucleic acids Proteins 0.000 description 1
- 102000039446 nucleic acids Human genes 0.000 description 1
- 150000007523 nucleic acids Chemical class 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920001542 oligosaccharide Polymers 0.000 description 1
- 150000002482 oligosaccharides Chemical class 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000006368 phosphonoyl group Chemical group [*:1]P([*:2])=O 0.000 description 1
- 125000005499 phosphonyl group Chemical group 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 125000005920 sec-butoxy group Chemical group 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000000707 stereoselective effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000005556 structure-activity relationship Methods 0.000 description 1
- 238000000859 sublimation Methods 0.000 description 1
- 230000008022 sublimation Effects 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 125000001544 thienyl group Chemical group 0.000 description 1
- 150000003569 thioglycosides Chemical class 0.000 description 1
- 125000000025 triisopropylsilyl group Chemical group C(C)(C)[Si](C(C)C)(C(C)C)* 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/02—Acyclic radicals, not substituted by cyclic structures
- C07H15/04—Acyclic radicals, not substituted by cyclic structures attached to an oxygen atom of the saccharide radical
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/18—Acyclic radicals, substituted by carbocyclic rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H15/00—Compounds containing hydrocarbon or substituted hydrocarbon radicals directly attached to hetero atoms of saccharide radicals
- C07H15/20—Carbocyclic rings
- C07H15/207—Cyclohexane rings not substituted by nitrogen atoms, e.g. kasugamycins
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
- C07H17/00—Compounds containing heterocyclic radicals directly attached to hetero atoms of saccharide radicals
- C07H17/04—Heterocyclic radicals containing only oxygen as ring hetero atoms
-
- 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
Definitions
- the present invention relates to a method for selectively producing a glycoside compound having a 1,2-one trans configuration.
- sugar chains have attracted much attention as the third in vivo polymer after nucleic acids and proteins. It has been clarified that sugar chains existing on the cell surface have various functions such as information transmission between cells and interaction with external matrices such as viruses. Elucidation of the structure-activity relationship of sugar chains Is an urgent issue. However, it is extremely difficult to separate and purify chemically pure glycan compounds from biological samples because glycan compounds exist on the cell surface as a heterogeneous mixture of different structures and binding positions. It is. For this reason, there is a strong demand for the supply of sugar chain compounds that have a well-defined chemical synthesis and are chemically pure.
- the 1,2-transglycoside bond is a typical glycoside bond often found in sugar chains.
- this stereoselective synthesis method of bonds has used an acyl group as a protecting group for the hydroxyl group at the 2-position, and has utilized the stereo-orientation effect based on this intramolecular involvement.
- the by-product of the orthoester has always been a problem.
- Non-patent Document 1 The present inventor has developed a continuous glycosylation reaction in which oligosaccharides are synthesized by repeating the same reaction using only thioglycoside. This method was extremely effective for sugar derivatives with an amino group at the 2-position, such as dalcosamine, but when sugar derivatives with a hydroxyl group at the 2-position, such as glucose and galactose, were used, Only the ester form was selectively produced and its isomerization to O-glycoside was extremely difficult.
- Non-Patent Document 1 Ang ew. Ch em. Int Ed. 2004, 43, 2 145
- An object of the present invention is to provide a method for selectively producing a 1,2-transglycoside compound by suppressing by-production of an orthoester in a sugar derivative having a hydroxyl group at the 2-position. Disclosure of the invention
- the present invention relates to the following 1,2-transglycoside compound production method and 2-phosphonoyl 1,2-transglycoside compound used in the production method.
- a glycoside compound from (a) a furanose compound or a pyranoose compound and (b) an alcohol compound, a furanose compound or substituent that may have a substituent in which the hydroxyl group at position 2 is protected with a group
- [1 2 and 11 3 represent the same or different alkyl group having 1 to 4 carbon atoms, or an aryl group that may have a substituent, or R 2 and R 3 are bonded to each other to form 2 carbon atoms.
- 4 represents an alkylene group (the alkylene group is an alkyl group having 1 to 4 carbon atoms) It may be substituted or via a phenylene group).
- m and n represent an integer of 0 or 1.
- the furanoic compound is alapofuranose, erythrofuranose, darcofuranose, ribofuranose, threofuranose or xylofuranose
- the pyranose compound is arabovillanose, altroviranose, darcopyranose, galactopyranose, glopyranose, man Nopyranose, lipopyranose, xylopyranose or darcopyranuronic acid, alcohol compound having 1 to 4 carbon atoms, alicyclic alcohol having 5 to 8 carbon atoms, aromatic alcohol, furanose, pyranose
- the 2-phosphonoyruol represented by the formula (3) is characterized in that the alcohol compound represented by the formula (2) is allowed to act on the 2-phosphonopyranose compound represented by the formula (1).
- a process for producing one transglycoside compound is characterized in that the alcohol compound represented by the formula (2) is allowed to act on the 2-phosphonopyranose compound represented by the formula (1).
- R 1 represents an alkyl group having 1 to 20 carbon atoms, an aryl group that may have a substituent, or a heteroaromatic group
- X represents a halogen atom.
- R 4 , R 5 and R 6 are the same or different and each represents a protecting group for a sugar hydroxyl group.
- E represents a methylene group or a carbonyl group. A is the same as above. ]
- Q 2 represents an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent at an arbitrary position, or the following group.
- L 1 is basic OA_OG, -N (J x ) (J 2 ).
- a 1 represents a group shown below
- G represents a protecting group for a sugar hydroxyl group
- J 1 and J 2 represent a protecting group for a hydrogen atom or an amino group.
- R 2 ′ and R 3 ′ are the same or different alkyl groups having 1 to 4 carbon atoms and aryl groups which may have a substituent, or R 2 ′ and R 3 ′ are bonded to each other to form carbon
- m ′ and n ′ are Represents an integer of 0 or 1.
- R 1 ′ is an alkyl group having 1 to 20 carbon atoms, an aryl group that may have a substituent, Represents a mouth aromatic group, 'represents a halogen atom
- G 1 represents a protecting group for a sugar hydroxyl group.
- R 7 , R 8 and R 9 are the same or different and each represents a protecting group for a sugar hydroxyl group.
- E 1 represents a methylene group or a force group.
- the 2-phosphonoylpyranose compound represented by the formula (1) is reacted with the alcohol compound represented by the formula (2 a) on the 2-phosphonoylpyranose compound represented by the formula (3 a). , 2-Transglycoside compound production method.
- Q 2a represents the following group.
- a 1 R 7 , R 8 , R 9 and E 1 are the same as above.
- a process comprising the step of allowing an alcohol compound to act at least once on a bisphosphonoluene 1,2-transdalicoside compound represented by the formula (3a). Compound production method.
- Q 4 represents an alkyl group having 1 to 4 carbon atoms, a cycloalkyl group having 5 to 8 carbon atoms which may have a substituent at an arbitrary position, or the following group.
- L 2 is a group —OH, —OG, —N (J 1 ) (J 2 ). ⁇ ⁇ , R 7 , R 8 , R 9 , E 1 , G, JJ 2 are the same as above. ]
- alkyl group having 1 to 4 carbon atoms examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isoptyl group, a sec-butyl group, and a tert-butyl group.
- Examples of the aryl group include a phenyl group and a naphthyl group.
- the aryl group may have a substituent at any position.
- Examples of the substituent include a halogen atom, Examples thereof include alkyl groups having 1 to 4 carbon atoms.
- Specific examples of the halogen atom include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom. These substituents may be the same or different and may be substituted from 1 to a substitutable number.
- alkylene group having 2 to 4 carbon atoms examples include a dimethylene group, a trimethylene group, and a tetramethylene group, which may be substituted with an alkyl group having 1 to 4 carbon atoms at any position, and via a phenylene group. It may be.
- group — (CH 2 ) 2 , group 1 (CH 2 ) 3 —, group 1 (CH 2 ) 4 —, group _C (CH 3 ) 2 C (CH 3 ) 2 —, group 1 CH 2 CH (CH 3 ) CH 2 —, group _CH (CH 3 ) CH 2 CH (CH 3 ) 1, group 1 C (CH 3 ) 2 CH 2 CH 2 —, group — CH 2 C (CH 3 ) 2 CH 2 _, _CH 2 CH 2 — C 6 H 4 — CH 2 — etc. can be exemplified.
- alkoxy group examples include alkoxy groups having 1 to 4 carbon atoms such as a methoxy group, an ethoxy group, an n-propoxy group, an isopropyl group, an n-butoxy group, an isobutoxy group, a sec-butoxy group, and a tert-butoxy group.
- alkenyloxy group examples include C2-C4 alkenyloxy groups such as a vinyloxy group, a propenyloxy group, and a butenyloxy group.
- the protecting group for the sugar hydroxyl group is not particularly limited as long as it is used as a protecting group for the hydroxyl group of the sugar compound.
- a benzyl group a methoxymethyl group, a tert-butyldimethylsilyl group, a triisopropyl silyl group.
- a ring may be formed by a methylene group, an ethylene group, an isopropylidene group, or a benzylidene group with respect to two adjacent hydroxyl groups.
- Examples of the cycloalkyl group having 5 to 8 carbon atoms include cyclopentyl, cyclohexyl, cycloheptyl, and cyclooctyl, and may have a substituent at any position.
- Examples of the substituent include alkyl groups having 1 to 4 carbon atoms. Specifically, 4,5-dimethylpentyl, 4-methylhexyl, 3,5-monodimethylhexyl, 4-tert- Examples include butyl hexyl, 2, 4, 6-trimethyl hexyl and the like.
- any furanose compound having a hydroxyl group at the 2-position can be used without any particular limitation.
- arapofuranose, erythrofuranos, dalcofuranos, ribofuranose, leuofuranos or xylofuranos can be used.
- These furanose compounds may have a substituent, and examples of the substituent include a group composed of a monosaccharide or a polysaccharide which may be protected with a sugar hydroxyl protecting group and a sugar hydroxyl protecting group. it can.
- the bilanose compound is not particularly limited as long as it is a pyranose compound having a hydroxyl group at the 2-position.
- These pyranose compounds may have a substituent, and examples of the substituent include a group consisting of a monosaccharide or a polysaccharide which may be protected with a sugar hydroxyl protecting group or a sugar hydroxyl protecting group. Can do. .
- the groups (A-3) and (A-5) are particularly preferably used.
- a pyranose compound in which the hydroxyl group at position 2 is protected with a group A can be produced by reacting a pyranoose compound with a phosphate halide compound represented by the formula (5).
- a 2-phosphonoyl 1,2-transpyranose compound represented by the formula (1) can be produced according to the following reaction formula 1-1.
- Reaction Formula-1 by reacting the pyranose compound represented by the formula (6-1), (6-2), (6-3) with the phosphate halide represented by the formula (5), the formula ( expression corresponding to the compound represented by 1) (1- Q 1 - 1 ), (1 -Q 1 - 2), (1 one Q 1 - 3) represented by 2 _ Hosuhonoiru - 1, 2 - trans A pyranose compound can be produced.
- This reaction is usually carried out in a solvent. After the base is allowed to act on the pyranose compound represented by the formulas (6-1), (6-2), (6-3), it is represented by the formula (5). Makes phosphate halide act.
- the solvent used is not particularly limited as long as it is inert to the reaction.
- aliphatic hydrocarbons such as hexane, heptane, and pentane
- alicyclic hydrocarbons such as cyclohexane
- benzene Halogenated aromatic hydrocarbons such as toluene and xylene, dichloromethane, chloroform, 1,2-dichloroethane, 1,1,1-trichloroethane, tetrachloroethylene, trichloroethylene, carbon tetrachloride, chlorobenzene, dichlorobenzene, etc.
- Hydrocarbons Jetyl ether, Isopropyl ether, Tetrahydrofuran, Dioxane, Monoglyme, etc.
- Ethers N, N-dimethylformamide, N, N-dimethylacetamide, 1, 3—
- Examples thereof include amides such as dimethylimidazolidinone, sulfoxides such as dimethyl sulfoxide, and mixed solvents thereof.
- amides such as dimethylimidazolidinone
- sulfoxides such as dimethyl sulfoxide
- mixed solvents thereof Among these, ethers, amides, and sulfoxides are particularly preferable.
- the amount of these solvents used is about 1 to 100 liters, preferably about 5 to 20 liters per kg of the pyranose compound represented by the formula (6-1), (6-2), or (6-3). do it.
- Examples of the base to be used include alkali metal carbonates such as sodium carbonate and potassium carbonate, alkali metal hydrides such as sodium hydride, organic bases such as triethylamine, pyridine and DBU, butyllithium, lithium diisopropylamide, lithium pith. Examples thereof include lithium salts such as trimethylsilylamide.
- bases can be used alone or in combination of two or more, and the amount used is 1 to 10 with respect to the pyranose compound represented by the formula (6-11-1), (6-2), (6-3). Equivalent, preferably :! ⁇ 5 equivalents should be used.
- the use ratio of the bilanose compound represented by the formulas (6-1), (6-2), and (6-3) and the phosphate halide represented by the formula (5) can be used at any ratio. However, the latter is preferably used in an amount of 1.0 to 2.0 molar equivalents relative to 1 mole of the former.
- the reaction temperature can be arbitrarily set in the range of ⁇ 20 to 100 ° C., preferably 0 to 30 ° C., and the reaction time is not particularly limited, but is usually about 30 minutes to 3 hours. .
- the 2-phosphonopyranose compound (1) obtained as described above and having a hydroxyl group at the 2-position protected with a phosphate ester is a novel compound not described in any literature.
- the pyranose compounds represented by the formulas (6-1), (6-2), and (6-3) can be produced by making use of conventionally known methods as described below, for example.
- Compound of formula (6-1) Glucose
- any alcohol compound that forms a glycosidic bond with the 1-position of pyranose can be used without particular limitation.
- linear or branched aliphatic alcohols such as methanol, ether, propanol, isopropanol, bubutanol, etc.
- carbons such as cyclohexanol, cyclopentanol, cyclopentanol, etc.
- Aliphatic alcohols of number 58 aromatic alcohols such as phenol, cresol, naphthol, arabofuranose, erythrofuranose, darcofuranos, galac ⁇ furanose, fructofuranose, ribofuranose, deo Pyranoses such as xylipofuranos, thorefuranos, xylofuranose, etc., arapopiranos, arroviranose, darcopyranose, galactopyranose, gloviranose, mannopyranose, lipopyranose, xylopyranose, darcopyranuronic acid , 2-amino _ 2-deoxy galactopyranose, 2-amino-2-deoxyglucopyranose, etc., aminobilanoses, dalcosane and other anhydrosaccharides, gentiobiose, sucrose, cellobiose, lactose, aralacose, maltose, Polysaccharides
- R 1 represents an alkyl group having 1 to 20 carbon atoms, an aryl group that may have a substituent, or a heteroaromatic group
- X represents a halogen atom.
- alkyl group having 1 to 20 carbon atoms examples include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, an n-butyl group, an isobutyl group, a sec-butyl group, a tert_butyl group, a hexyl group, Examples include octyl, decyl, dodecyl, hexadecyl, octyldecyl, and eicosyl groups.
- the aryl group which may have a substituent is the same as described above.
- the heteroaromatic group examples include a pyridyl group.
- the alcohol compound represented by the formula (2) After activating the 2-phosphonylpyranose compound represented by the formula (1) as a pyranose compound in which the 2-position hydroxyl group is protected with the group A, the alcohol compound represented by the formula (2) is allowed to act as the alcohol compound.
- the 2_phosphonoyl_1,2-transglycoside compound represented by the formula (3) can be produced.
- Z is a basic S -... If it is R 1 or a group one SO- R 1, for example, J. Am C h em S o c , 20 01, 123, 901 5 Ya '' Ca rb ohyd ratesin Ch em istry and B iolo gy " , Wiley— After activating the 2-phosphonopyranose compound represented by formula (1) according to VCH, 2000, Vol. 1, Ch ap 4 (pp 93-134), The alcohol compound represented can be reacted.
- This reaction is carried out in a solvent.
- the solvent used include halogenated hydrocarbons such as dichloromethane, dichloroethane, and tetrachloroethane, and aromatic hydrocarbons such as toluene, but dichloromethane is tetrachloroethane. Should be anhydrous to the extent that it does not affect the reaction.
- the amount of the solvent used may be about 1 to 100 liters, preferably about 5 to 50 liters per kilogram of compound (1).
- Compound (1) is activated by the action of 2,6-tert-butyl 4-methylpyridine (D TBMP), benzenesulfinyl piperidine (BSP), trifluoromethane anhydride sulfonic acid (T f 2 0), etc. Is called.
- D TBMP 2,6-tert-butyl 4-methylpyridine
- BSP benzenesulfinyl piperidine
- T f 2 0 trifluoromethane anhydride sulfonic acid
- the amount of DT BMP is 1-5 molar equivalents, the amount of B SP 1-2 equivalents, the amount of T f 2 0 1-2 and equivalents It ’s good.
- This reaction is preferably carried out in an anhydrous system, preferably in the presence of a dehydrating agent such as molecular sieve (Molecular sieve 4A).
- a dehydrating agent such as molecular sieve (Molecular sieve 4A).
- This reaction is preferably performed at a low temperature of 140 ° C. or lower because the thermal stability of the active species generated in the middle is low.
- the amount of the alcohol compound (2) used may be 0.8 to 3 mole equivalents, preferably 1.0 to 2.0 mole equivalents per mole of the compound (1).
- the reaction temperature can be arbitrarily set in the range of 80 to 40 ° C, and is usually preferably 70 to 45 ° C, and the reaction time is not particularly limited, but is usually about 1 minute to 1 hour. Good.
- the 2-phosphonopyranose compound represented by the formula (1) can be activated, for example, according to the description in the following literature.
- the 1,2--lance-type bilanose compound glanose compound is conventionally used.
- the production of orthoester compounds by-produced in the lycosylation reaction can be suppressed, and 1,2-one transglycoside compounds can be produced with extremely high selectivity.
- the present invention relates to a 2-phosphonoylpyranose compound (I or III) in which a specific phosphate ester compound is used as a protecting group, and the 2-position hydroxyl group of the pyranose compound is protected with the protecting group (A).
- a specific phosphate ester compound is used as a protecting group
- the 2-position hydroxyl group of the pyranose compound is protected with the protecting group (A).
- the alcohol compound represented by the formula (2) the steric bond between the 0-glycoside bond at the 1st position on the pyranose ring of the 0-glycoside compound ( ⁇ or IV) and the protected hydroxyl group at the 2nd position.
- the arrangement can be a transformer arrangement with high selectivity. Furthermore, this stereoselectivity can be maintained without being greatly affected by the type of alcohol compound to be acted on.
- the 2-phosphonoyl 1,2-transglycoside compound represented by the formula (3) produced by this production method includes the 2-phosphonoyl _ 1,2-transglycoside compound represented by the formula (3a). It is possible to form a new glycoside bond by using an alcohol compound. If the alcohol compound to be acted on is, for example, the alcohol compound represented by the formula (2a), it is possible to further form a glycosidic bond, and the sugar chain can be arbitrarily extended according to the number of repetitions.
- the 2-phosphonoleu 1,2--lance glycoside compound represented by the formula (3) obtained above and the 2-phosphonoleu 1,2-trans glycoside compound represented by the formula (3 a) are not described in the literature. It is a novel compound.
- the protecting group A at the 2-position hydroxyl group can be easily removed from the various glycoside compounds obtained.
- reaction formula 1 3 a base is allowed to act on the 2-phosphonoyl 1,2-transglycoside compound represented by the formula (3), thereby removing the group A. 1,2-transglycoside compounds can be produced.
- Examples of the base to be used include alkali metal alkoxides such as sodium methoxide, sodium ethoxide and potassium t-butoxide, and alkali metal hydroxides such as sodium hydroxide and lithium hydroxide.
- bases can be used alone or in combination of two or more, and the amount used is 1 to 10 equivalents, preferably 2.0 to 5.0 equivalents, relative to compound (3).
- This reaction is carried out in a solvent, and examples of the solvent used include alcohols such as methanol, ethanol and isopropanol, water or a mixed solvent thereof, or a mixed solvent of water, alcohol and tetrahydrofuran, dioxane or the like. It is possible.
- the amount of these solvents used may be about 1 to 100 liters, preferably about 5 to 20 liters, per 1 kg of compound (3).
- the reaction temperature can be arbitrarily set within the range of 0 ° C to the boiling point of the solvent, and is usually room temperature. To about 60 ° C is preferred.
- the reaction time is not particularly limited, but usually about 0.5 to 10 hours is sufficient.
- part means “part by weight” unless otherwise specified.
- SPh is a thiophenyl group
- Bn is a benzyl group
- TBS is a tert-butyldimethylsilyl group
- c-He X is a cyclohexyl group
- Ph is a phenyl group
- TCPN is a tetrachlorophthaloyl group.
- the organic layer is separated, the aqueous layer is extracted with ethyl acetate, and all the extracted organic layers are washed with saturated brine. Then, after drying over magnesium sulfate, filtration is performed, and the filtrate is subjected to distillation of the organic solvent under reduced pressure using a rotary evaporator to obtain a crude product.
- 2-Phosphonylthiophenyl dalcoside compound (6 3.9 mg, 0.09 mm ol), BS P (20.9 mg, 0.10 mm o 1) and DTB MP (39. Omg) prepared in Example 1 , 0.1 8 mmo 1) and about 90 mg of molecular sieves
- the 2-phosphonoyl 1,2-glycoside compound (20.5111, 0.01 811111101) prepared in Example 21 was mixed with 1,4-dioxane (0.50 m 1) sodium (7 ⁇ 6 mg, 0. 33 lmmo 1) solution was added at room temperature, and after 2 hours, the reaction mixture was neutralized with saturated aqueous ammonium chloride solution. The organic layer was separated and the water tank was extracted three times with ethyl acetate. The extract was combined with the organic layer, washed with saturated brine, dried over magnesium sulfate, and concentrated under reduced pressure to give a residue (20.5 mg). The residue is an alcohol form from which the 2-position phosphonyl group has been removed.
- the obtained residue was purified by flash column chromatography (silicc agel 1.0 g; elu ti on w i th 30% et al l acet e te in h x a n e) to obtain a 2-acetoxyglycoside compound.
- a specific phosphate ester (phosphonoyl group) as a protecting group for the 2-position hydroxyl group of a furanose compound or a pyranose compound can be selectively used as a sugar donor in a glycosylation reaction.
- _Trans-type glycosidic bonds can be formed, and the generation of by-products corresponding to orthoesters can be suppressed.
- sugar chains can be arbitrarily extended.
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Abstract
Description
Claims
Priority Applications (5)
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JP2007503808A JP4762973B2 (ja) | 2005-02-18 | 2006-02-20 | 1,2−トランスグリコシド化合物の製造方法 |
CN2006800037546A CN101111507B (zh) | 2005-02-18 | 2006-02-20 | 1,2-反式糖苷化合物的制造方法 |
US11/884,544 US8212013B2 (en) | 2005-02-18 | 2006-02-20 | Process for producing 1,2-trans-glycoside compound |
EP06714658A EP1849794A4 (en) | 2005-02-18 | 2006-02-20 | PROCESS FOR THE SYNTHESIS OF A 1,2-TRANS-GLYCOSIDE DERIVATIVE |
US13/477,950 US8664372B2 (en) | 2005-02-18 | 2012-05-22 | Process for producing 1,2-trans-glycoside compound |
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JP2005043220 | 2005-02-18 | ||
JP2005-043220 | 2005-02-18 |
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US11/884,544 A-371-Of-International US8212013B2 (en) | 2005-02-18 | 2006-02-20 | Process for producing 1,2-trans-glycoside compound |
US13/477,950 Division US8664372B2 (en) | 2005-02-18 | 2012-05-22 | Process for producing 1,2-trans-glycoside compound |
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EP (1) | EP1849794A4 (ja) |
JP (1) | JP4762973B2 (ja) |
KR (1) | KR100966986B1 (ja) |
CN (1) | CN101111507B (ja) |
TW (1) | TWI331609B (ja) |
WO (1) | WO2006088256A1 (ja) |
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WO2008055964A1 (de) * | 2006-11-09 | 2008-05-15 | Rheinisch-Westfälische Technische Hochschule Aachen | Verfahren zur herstellung von cyclischen phosphinen oder bisphosphinen, cyclische phosphonate von optisch aktiven diolen und deren herstellung |
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FR2935975B1 (fr) * | 2008-09-16 | 2010-12-17 | Sanofi Aventis | Procede de preparation du 1,6:2,3-dianhydro-b-d- mannopyranose. |
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2006
- 2006-02-20 CN CN2006800037546A patent/CN101111507B/zh not_active Expired - Fee Related
- 2006-02-20 KR KR1020077021258A patent/KR100966986B1/ko not_active IP Right Cessation
- 2006-02-20 TW TW095105697A patent/TWI331609B/zh not_active IP Right Cessation
- 2006-02-20 EP EP06714658A patent/EP1849794A4/en not_active Withdrawn
- 2006-02-20 WO PCT/JP2006/303519 patent/WO2006088256A1/ja active Application Filing
- 2006-02-20 JP JP2007503808A patent/JP4762973B2/ja not_active Expired - Fee Related
Non-Patent Citations (5)
Title |
---|
CRICH D. ET AL.: "Chemistry of beta-(Phosphatoxy) alkyl and beta-(Acyloxy)alkyl Radicals", J. AM. CHEM. SOC., vol. 117, no. 46, 1995, pages 11455 - 11470, XP003002305 * |
KOCH A. ET AL.: "Radical rearrangement of 2-O-(diphenylphosphoryl)glycosyl bromides", J. ORG. CHEM., vol. 58, no. 5, 1993, pages 1083 - 1089, XP001062151 * |
KOCH A. ET AL.: "Radical rearrangements of 2-O-(diphenoxyphosphoryl)glycosyl bromides", HELV. CHIM. ACTA, vol. 76, no. 4, 1993, pages 1687 - 1701, XP003002306 * |
RABUKA D. ET AL.: "Synthesis and NMR characterization of the six regioisomeric monophosphates of octyl beta-D-galactopyranosyl-(1 4)-2-acetamido-2-deoxy-beta-D-glucopyranoside", CARBOHYDR. RES., vol. 337, no. 21 TO 23, 2002, pages 2127 - 2151, XP004392207 * |
See also references of EP1849794A4 * |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
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WO2008055964A1 (de) * | 2006-11-09 | 2008-05-15 | Rheinisch-Westfälische Technische Hochschule Aachen | Verfahren zur herstellung von cyclischen phosphinen oder bisphosphinen, cyclische phosphonate von optisch aktiven diolen und deren herstellung |
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JPWO2006088256A1 (ja) | 2008-07-17 |
KR20070103075A (ko) | 2007-10-22 |
JP4762973B2 (ja) | 2011-08-31 |
CN101111507A (zh) | 2008-01-23 |
EP1849794A4 (en) | 2012-08-08 |
KR100966986B1 (ko) | 2010-06-30 |
EP1849794A1 (en) | 2007-10-31 |
TWI331609B (en) | 2010-10-11 |
CN101111507B (zh) | 2011-08-31 |
TW200700428A (en) | 2007-01-01 |
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