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【结 构 式】 
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【分子编号】58146 【品名】(2R,4aR,6R,7R,8R,8aS)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(1R,2S,3R,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]oct-2-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-7,8-dimethoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine; (2R,4aR,6R,7R,8R,8aS)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(1R,2S,3R,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]oct-2-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-8-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl methyl ether 【CA登记号】 |
【 分 子 式 】C50H80O25 【 分 子 量 】1081.1702 【元素组成】C 55.55% H 7.46% O 37% |
合成路线1
该中间体在本合成路线中的序号：(X)Coupling between trisaccharide (XIII) and thioglycoside (VII) using N-iodosuccinimide/trifluoromethanesulfonic acid furnishes pentasaccharide (XIV). After methanolysis of the benzoate esters of (XIV), the poly-methyl ether (XV) is prepared by methylation of (XIV) with iodomethane and NaH. Acidic hydrolysis of the benzylidene acetal (XV), followed by selective esterification with 1-(benzoyloxy)-benzotriazole affords benzoate (XVI).
| 【1】 Petitou, M.; Herbert, J.-M.; Duchaussoy, P.; Basten, J.; Dreef-Tromp, C.; Driguez, P.-A.; Van Boeckel, C. (Akzo Nobel N.V.; Sanofi-Synthélabo); Synthetic polysaccharides, their method of production and pharmaceutical compsns. containing same. EP 1049721; FR 2773804; US 6528497; WO 9936443 . |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VII) | 58138 | (2R,4aR,6R,7R,8S,8aR)-7-(benzoyloxy)-6-{[(2R,3S,4S,5R,6S)-4,5-bis(benzoyloxy)-2-[(benzoyloxy)methyl]-6-(ethylsulfanyl)tetrahydro-2H-pyran-3-yl]oxy}-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl benzoate | C56H50O15S | 详情 | 详情 | |
| (VIII) | 58144 | ((2R,3S,4S,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(1R,2S,3R,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]oct-2-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-yl)methyl benzoate | C32H48O16 | 详情 | 详情 | |
| (IX) | 58145 | ((2R,3S,4R,5R,6R)-3-({(2S,3R,4S,5R,6R)-5-{[(2R,4aR,6R,7R,8S,8aR)-7,8-bis(benzoyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy}-3,4-bis(benzoyloxy)-6-[(benzoyloxy)methyl]tetrahydro-2H-pyran-2-yl}oxy)-6-{[(2R,3S,4R,5R,6R)-6-{[(1R,2S,3R,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]oct-2-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxytetrahydro-2H-pyran-2-yl)methyl benzoate | C86H92O31 | 详情 | 详情 | |
| (X) | 58146 | (2R,4aR,6R,7R,8R,8aS)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(1R,2S,3R,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]oct-2-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-7,8-dimethoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine; (2R,4aR,6R,7R,8R,8aS)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(1R,2S,3R,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]oct-2-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-8-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-7-yl methyl ether | C50H80O25 | 详情 | 详情 | |
| (XI) | 58147 | ((2R,3S,4S,5R,6R)-6-{[(2R,3S,4R,5R,6S)-6-{[(2R,3S,4R,5R,6R)-6-{[(2R,3S,4R,5R,6R)-6-{[(1R,2S,3R,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]oct-2-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-4,5-dimethoxy-2-(methoxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-3-hydroxy-4,5-dimethoxytetrahydro-2H-pyran-2-yl)methyl benzoate | C50H80O26 | 详情 | 详情 |