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【结 构 式】 
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【分子编号】42066 【品名】ethyl 5-[(3aS,4R,5R,6aS)-5-(acetoxy)-4-[(1S,2E)-1-(acetoxy)-2-octenyl]hexahydro-2(1H)-pentalenylidene]pentanoate 【CA登记号】 |
【 分 子 式 】C27H42O6 【 分 子 量 】462.62688 【元素组成】C 70.1% H 9.15% O 20.75% |
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：(V)The cyclization of undecadienedioic acid diethyl ester (I) with 2(E)-octenal (II) by means of ClTi(OiPr)3 gives the pentalenone derivative (III), which is reduced with NaBH4 in methanol, yielding alcohol (IV) after chromatographic purification. The acylation of (IV) with Ac2O and pyridine affords the diacetate (V), which is rearranged with a catalytic amount of PdCl2(CH3CN)2 in THF to provide the diacetate (VI). Finally, this compound is hydrolyzed with LiOH in methanol.
| 【1】 Okamoto, S.; et al.; Highly stereocontrolled synthesis of carbacyclin from acyclic starting materials via Ti(II)-mediated tandem cyclization. J Am Chem Soc 2000, 122, 45, 11244. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (I) | 42062 | diethyl (3E,6E)-6-allyl-3,6-undecadienedioate | C18H28O4 | 详情 | 详情 | |
| (II) | 42063 | trans-2-octenal; (E)-2-octenal | 2548-87-0 | C8H14O | 详情 | 详情 |
| (III) | 42064 | ethyl 5-[(3aS,4S,6aS)-4-[(1S,2E)-1-hydroxy-2-octenyl]-5-oxohexahydro-2(1H)-pentalenylidene]pentanoate | C23H36O4 | 详情 | 详情 | |
| (IV) | 42065 | ethyl 5-[(3aS,4R,5R,6aS)-5-hydroxy-4-[(1S,2E)-1-hydroxy-2-octenyl]hexahydro-2(1H)-pentalenylidene]pentanoate | C23H38O4 | 详情 | 详情 | |
| (V) | 42066 | ethyl 5-[(3aS,4R,5R,6aS)-5-(acetoxy)-4-[(1S,2E)-1-(acetoxy)-2-octenyl]hexahydro-2(1H)-pentalenylidene]pentanoate | C27H42O6 | 详情 | 详情 | |
| (VI) | 42067 | ethyl 5-[(3aS,4S,5R,6aS)-5-(acetoxy)-4-[(E,3S)-3-(acetoxy)-1-octenyl]hexahydro-2(1H)-pentalenylidene]pentanoate | C27H42O6 | 详情 | 详情 |
Extended Information