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【结 构 式】 
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【分子编号】52849 【品名】(2E,4E,6E,8E)-2,4,6,8-decatetraenedioyl dichloride 【CA登记号】 |
【 分 子 式 】C10H8Cl2O2 【 分 子 量 】231.07772 【元素组成】C 51.98% H 3.49% Cl 30.68% O 13.85% |
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：(XXIII)The second epoxide function was introduced into (XVIII) upon treatment with m-chloroperbenzoic acid, yielding (XIX). Oxidation of the primary alcohol of (XIX) to aldehyde (XX) was effected by means of Dess-Martin periodinane reagent. Subsequent Wittig reaction of aldehyde (XX) with isopropylidene triphenylphosphorane furnished olefin (XXI). The chiral fumagillol (-)-(XXII) was then obtained by hydrolysis of the benzoate ester (XXI) in the presence of methanolic K2CO3. Finally, condensation of alcohol (-)-(XXII) with the acid chloride (XXIII) led to the title compound.
| 【1】 Taber, D.F.; et al.; Synthesis of (-)-fumagillin. J Am Chem Soc 1999, 121, 23, 5589. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XVIII) | 52845 | (3R,4S,5S,6R)-4-[(E)-4-hydroxy-1-methyl-1-butenyl]-5-methoxy-1-oxaspiro[2.5]oct-6-yl benzoate | C20H26O5 | 详情 | 详情 | |
| (XIX) | 52846 | (3R,4S,5S,6R)-4-[(2R,3R)-3-(2-hydroxyethyl)-2-methyloxiranyl]-5-methoxy-1-oxaspiro[2.5]oct-6-yl benzoate | C20H26O6 | 详情 | 详情 | |
| (XX) | 52847 | (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(2-oxoethyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl benzoate | C20H24O6 | 详情 | 详情 | |
| (XXI) | 52848 | (3R,4S,5S,6R)-5-methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]oct-6-yl benzoate | C23H30O5 | 详情 | 详情 | |
| (XXII) | 13712 | (3R,4S,5S,6R)-5-Methoxy-4-[(2R,3R)-2-methyl-3-(3-methyl-2-butenyl)oxiranyl]-1-oxaspiro[2.5]octan-6-ol | C16H26O4 | 详情 | 详情 | |
| (XXIII) | 52849 | (2E,4E,6E,8E)-2,4,6,8-decatetraenedioyl dichloride | C10H8Cl2O2 | 详情 | 详情 |
Extended Information