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【结 构 式】 
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【分子编号】48951 【品名】(2S,3R,4S,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-(phenylsulfanyl)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate 【CA登记号】 |
【 分 子 式 】C48H60O13SSi 【 分 子 量 】905.1481 【元素组成】C 63.69% H 6.68% O 22.98% S 3.54% Si 3.1% |
合成路线1
该中间体在本合成路线中的序号：(XIX)Synthesis of intermediate disaccharide (XX): The condensation of intermediate monosaccharide (VIII) with intermediate acetimidate (XVIII) by means of BF3/Et2O gives the disaccharide (XIX), which is converted into the desired acetimidate (XX) by reaction with NBS and trichloroacetonitrile and DBU in dichloromethane/water.
| 【1】 Jin, Z.; Yu, W.; A new strategy for the stereoselective introduction of steroid side chain via alpha-alkoxy vinyl cuprates: Total synthesis of a highly potent antitumor natural product OSW-1. J Am Chem Soc 2001, 123, 14, 3369. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 48942 | (2S,3R,4R,5S)-4-hydroxy-2-(phenylsulfanyl)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl acetate | C19H30O5SSi | 详情 | 详情 | |
| (XVIII) | 48950 | (3R,4S,5R)-4,5-bis[(4-methoxybenzyl)oxy]-2-[(2,2,2-trichloroethanimidoyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C31H32Cl3NO9 | 详情 | 详情 | |
| (XIX) | 48951 | (2S,3R,4S,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-(phenylsulfanyl)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C48H60O13SSi | 详情 | 详情 | |
| (XX) | 48952 | (2S,3R,4S,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[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C44H56Cl3NO14Si | 详情 | 详情 |
合成路线2
该中间体在本合成路线中的序号：(XIX)Intermediate beta-disaccharide trichloroacetimidate (XX): The glycosylation of intermediate (VIII) with intermediate (XVIII) by means of BF3/Et2O in dichloromethane gives the beta-disaccharide (XIX), which is converted into the target trichloroacetimidate (XX) by reaction with NBS, Cl3C-CN and DBU in dichloromethane
| 【1】 Yu, W.; Jin, Z.; Total synthesis of the anticancer natural product OSW-1. J Am Chem Soc 2002, 124, 23, 6576. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (VIII) | 48942 | (2S,3R,4R,5S)-4-hydroxy-2-(phenylsulfanyl)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl acetate | C19H30O5SSi | 详情 | 详情 | |
| (XVIII) | 48950 | (3R,4S,5R)-4,5-bis[(4-methoxybenzyl)oxy]-2-[(2,2,2-trichloroethanimidoyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C31H32Cl3NO9 | 详情 | 详情 | |
| (XIX) | 48951 | (2S,3R,4S,5R)-2-([(2S,3R,4R,5S)-3-(acetoxy)-2-(phenylsulfanyl)-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl]oxy)-4,5-bis[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C48H60O13SSi | 详情 | 详情 | |
| (XX) | 60151 | (2S,3R,4S,5R)-2-({(2S,3R,4R,5S)-3-(acetyloxy)-2-[(2,2,2-trichloroethanimidoyl)oxy]-5-[(triethylsilyl)oxy]tetrahydro-2H-pyran-4-yl}oxy)-4,5-bis[(4-methoxybenzyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C44H56Cl3NO14Si | 详情 | 详情 |