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【结 构 式】 
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【分子编号】58143 【品名】(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}-2-(hydroxymethyl)-4,5-dimethoxytetrahydro-2H-pyran-3-ol 【CA登记号】 |
【 分 子 式 】C25H44O15 【 分 子 量 】584.61536 【元素组成】C 51.36% H 7.59% O 41.05% |
合成路线1
该中间体在本合成路线中的序号：(XII)The known disaccharide thioglucoside (VI) is esterified by means of benzoyl chloride and pyridine to give the penta-benzoate (VII). Coupling between thioglycoside (VII) and 2,3-di-O-methyl-1,6-anhydro-D-glucose (VIII) is effected by treatment with N-iodosuccinimide and trifluoromethanesulfonic acid, yielding trisaccharide (IX). After methanolysis of the benzoate esters, the resultant penta-hydroxy compound (X) is alkylated with iodomethane and NaH, leading to the corresponding methyl ether (XI). Hydrolysis of the benzylidene acetal of (XI) with 80% AcOH provides diol (XII). The primary hydroxyl group of (XII) is then selectively esterified by using 1-(benzoyloxy)-benzotriazole to produce the mono-benzoate (XIII).
| 【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 |
|---|---|---|---|---|---|---|
| (VI) | 58137 | (2R,4aR,6R,7R,8R,8aS)-6-{[(2R,3S,4R,5R,6S)-6-(ethylsulfanyl)-4,5-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol | C21H30O10S | 详情 | 详情 | |
| (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) | 58139 | (1R,2S,3S,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]octan-2-ol | C8H14O5 | 详情 | 详情 | |
| (IX) | 58140 | (2R,4aR,6R,7R,8S,8aR)-7-(benzoyloxy)-6-[((2R,3R,4S,5R,6R)-4,5-bis(benzoyloxy)-2-[(benzoyloxy)methyl]-6-{[(1R,2S,3R,4R,5R)-3,4-dimethoxy-6,8-dioxabicyclo[3.2.1]oct-2-yl]oxy}tetrahydro-2H-pyran-3-yl)oxy]-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl | C62H58O20 | 详情 | 详情 | |
| (X) | 58141 | (2R,4aR,6R,7R,8R,8aS)-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-dihydroxy-2-(hydroxymethyl)tetrahydro-2H-pyran-3-yl]oxy}-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diol | C27H38O15 | 详情 | 详情 | |
| (XI) | 58142 | (2R,4aR,6R,7R,8R,8aS)-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}-7-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-8-yl methyl ether; (2R,4aR,6R,7R,8R,8aS)-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}-7,8-dimethoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine | C32H48O15 | 详情 | 详情 | |
| (XII) | 58143 | (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}-2-(hydroxymethyl)-4,5-dimethoxytetrahydro-2H-pyran-3-ol | C25H44O15 | 详情 | 详情 | |
| (XIII) | 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 |