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【结 构 式】 
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【分子编号】62651 【品名】(3aR,9R,9aR,9bS)-9-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-a]indolizin-6(4H)-one 【CA登记号】 |
【 分 子 式 】C11H17NO4 【 分 子 量 】227.26032 【元素组成】C 58.14% H 7.54% N 6.16% O 28.16% |
与该中间体有关的原料药合成路线共 1 条
合成路线1
该中间体在本合成路线中的序号：(XXVII)The reaction of (XXIV) with Ms-Cl and TEA in dichloromethane gives the mesylate (XXV), which is cyclized by means of K2CO3 in hot dioxane to yield the perhydroindolizinone (XXVI). The reductive debenzylation of (XXVI) with H2 over Pd/C in ethanol affords the hydroxy-perhydroindolizinone (XXVII), which is finally reduced with BH3/Me2S in THF to provide the target swainsonine acetonide (XXVIII) intermediate.
| 【1】 Honda, T.; et al.; Enantioselective synthesis of indolizidine alkaloids: Formal synthesis of (-)-swainsonine and of (+)-pumiliotoxin 251D. J Chem Soc - Perkins Trans I 1994, 15, 2091. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XXIV) | 62648 | (5R,6R)-5-(benzyloxy)-6-[(4S,5R)-5-(hydroxymethyl)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-piperidinone | C18H25NO5 | 详情 | 详情 | |
| (XXV) | 62649 | {(4R,5S)-5-[(2R,3R)-3-(benzyloxy)-6-oxopiperidinyl]-2,2-dimethyl-1,3-dioxolan-4-yl}methyl methanesulfonate | C19H27NO7S | 详情 | 详情 | |
| (XXVI) | 62650 | (3aR,9R,9aR,9bS)-9-(benzyloxy)-2,2-dimethylhexahydro[1,3]dioxolo[4,5-a]indolizin-6(4H)-one | C18H23NO4 | 详情 | 详情 | |
| (XXVII) | 62651 | (3aR,9R,9aR,9bS)-9-hydroxy-2,2-dimethylhexahydro[1,3]dioxolo[4,5-a]indolizin-6(4H)-one | C11H17NO4 | 详情 | 详情 | |
| (XXVIII) | 62616 | (3aR,9R,9aR,9bS)-2,2-dimethyloctahydro[1,3]dioxolo[4,5-a]indolizin-9-ol | C11H19NO3 | 详情 | 详情 |
Extended Information