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【结 构 式】 
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【分子编号】48979 【品名】(2S,3R,4R,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-[(2,2,2-trichloroethanimidoyl)oxy]-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate 【CA登记号】 |
【 分 子 式 】C40H68Cl3NO12Si3 【 分 子 量 】945.59406 【元素组成】C 50.81% H 7.25% Cl 11.25% N 1.48% O 20.3% Si 8.91% |
合成路线1
该中间体在本合成路线中的序号：(XVII)Synthesis of intermediate disaccharide (XVII): The regioselective glycosylation of intermediate arabinose derivative (VI) with the intermediate acetimidate (XIII) by means of BF3/Et2O gives the disaccharide (XIV), which is silylated with Tes-OTf and lutidine in dichloromethane to yield the fully protected disaccharide (XV). Elimination of the benzyl protecting group of (XV) by hydrogenation with H2 over Pd/C in hot ethyl acetate affords the hemiacetal (XVI), which is converted into the target trichloroacetimidate (XVII) by reaction with trichloroacetonitrile and DBU in dichloromethane.
| 【1】 Deng, S.; et al.; First total synthesis of an exceptionally potent antitumor saponin, OSW-1. J Org Chem 1999, 64, 1, 202. |
| 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) | 48969 | (2S,3R,4S,5S)-2-(benzyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl acetate | C14H18O6 | 详情 | 详情 | |
| (XIII) | 48975 | (3R,4R,5R)-2-[(2,2,2-trichloroethanimidoyl)oxy]-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C27H44Cl3NO7Si2 | 详情 | 详情 | |
| (XIV) | 48976 | (2S,3R,4R,5R)-2-[[(2S,3R,4S,5S)-3-(acetoxy)-2-(benzyloxy)-5-hydroxytetrahydro-2H-pyran-4-yl]oxy]-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C39H60O12Si2 | 详情 | 详情 | |
| (XV) | 48977 | (2S,3R,4R,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-(benzyloxy)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C45H74O12Si3 | 详情 | 详情 | |
| (XVI) | 48978 | (2S,3R,4R,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-hydroxy-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C38H68O12Si3 | 详情 | 详情 | |
| (XVII) | 48979 | (2S,3R,4R,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-[(2,2,2-trichloroethanimidoyl)oxy]-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C40H68Cl3NO12Si3 | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XVII)Final assembly of the target compound: The condensation of the intermediate aglycon (XXXII) with the intermediate disaccharide (XVII) by means of Tms-OTf in dichloromethane gives the protected adduct (XXXIII), which is finally treated with Pd(MeCN)2Cl2 in acetone/water to obtain the target saponin, OSW-1.
| 【1】 Deng, S.; et al.; First total synthesis of an exceptionally potent antitumor saponin, OSW-1. J Org Chem 1999, 64, 1, 202. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVII) | 48979 | (2S,3R,4R,5R)-2-([(3R,4R,5S)-3-(acetoxy)-2-[(2,2,2-trichloroethanimidoyl)oxy]-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C40H68Cl3NO12Si3 | 详情 | 详情 | |
| (XXXII) | 48964 | (3S,10R,13S,16S,17S)-3-[[tert-butyl(dimethyl)silyl]oxy]-17-[(1S)-1-(2-isopentyl-1,3-dioxolan-2-yl)ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthrene-16,17-diol | C35H62O5Si | 详情 | 详情 | |
| (XXXIII) | 48989 | (2S,3R,4R,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-([(3S,10R,13S,16S,17S)-3-[[tert-butyl(dimethyl)silyl]oxy]-17-hydroxy-17-[(1S)-1-(2-isopentyl-1,3-dioxolan-2-yl)ethyl]-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-16-yl]oxy)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C73H128O16Si4 | 详情 | 详情 |