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【结 构 式】 
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【分子编号】48974 【品名】(3R,4R,5R)-2-hydroxy-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate 【CA登记号】 |
【 分 子 式 】C25H44O7Si2 【 分 子 量 】512.79116 【元素组成】C 58.56% H 8.65% O 21.84% Si 10.95% |
合成路线1
该中间体在本合成路线中的序号：(XII)Synthesis of intermediate monosaccharide (XIII): The reaction of D-xylose (VII) with benzyl alcohol and HCl (gas) gives the 1-O-benzyl-D-xylose (VIII), which is regioselectively acylated with 4-methoxybenzoyl chloride (IX) and pyridine to yield 1-O-benzyl-2-O-(4-methoxybenzoyl)-D-xylose (X). The silylation of (X) with Tes-Cl and imidazole in DMF affords the disilylated compound (XI), which is debenzylated by hydrogenation with H2 over Pd/C in ethyl acetate to provide 2-O-(4-methoxybenzoyl)-3,4-O-bis(triethylsilyl)-D-xylose (XII). Finally, this compound is converted into the target trichloroacetimidate (XIII) 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 |
|---|---|---|---|---|---|---|
| (VII) | 48970 | 2,3,4,5-Tetrahydroxypentanal; D-xylopyranose; D-(+)-Xylose; D-xylose; D-(+)-Wood Sugar; Xylose; Wood Sugar | 58-86-6 | C5H10O5 | 详情 | 详情 |
| (VIII) | 48971 | (3R,4S,5R)-2-(benzyloxy)tetrahydro-2H-pyran-3,4,5-triol | C12H16O5 | 详情 | 详情 | |
| (IX) | 22671 | 4-Methoxybenzoyl chloride; p-Methoxybenzoyl chloride; 4-Anisoyl chloride | 100-07-2 | C8H7ClO2 | 详情 | 详情 |
| (X) | 48972 | (3R,4S,5R)-2-(benzyloxy)-4,5-dihydroxytetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C20H22O7 | 详情 | 详情 | |
| (XI) | 48973 | (3R,4R,5R)-2-(benzyloxy)-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C32H50O7Si2 | 详情 | 详情 | |
| (XII) | 48974 | (3R,4R,5R)-2-hydroxy-4,5-bis[(triethylsilyl)oxy]tetrahydro-2H-pyran-3-yl 4-methoxybenzoate | C25H44O7Si2 | 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 |