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【结 构 式】 
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【分子编号】24528 【品名】(3aS,4S,5R,6aR)-5-hydroxy-4-[(1E,3S,5R)-3-hydroxy-5,9-dimethyl-1,8-decadienyl]hexahydro-2(1H)-pentalenone 【CA登记号】 |
【 分 子 式 】C20H32O3 【 分 子 量 】320.47228 【元素组成】C 74.96% H 10.06% O 14.98% |
合成路线1
该中间体在本合成路线中的序号：(XV)Ketone (XIII) is reduced with NaBH4 to the dienic alcohol (XIV). The hydrolysis of (XIV) with HCl in aqueous acetone gives the dihydroxyketone (XV), which is treated with dihydropyran and p-toluenesulfonic acid to afford the bistetrahydropyranyloxy derivative (XVI). The Wittig condensation of ketone (XVI) with 4-(methoxycarbonylbutyl)triphenylphosphonium bromide (XVII) by means of NaH in DMSO affords the protected carbacyclin (XVIII), which is deprotected with acetic acid in THF water yielding 17R-methyl-20-isopropylidenecarbacyclin methyl ester (XIX). Finally, this compound is saponified with KOH in aqueous methanol.
| 【1】 Kojima, K.; Sakai, K.; Kobayashi, S. (Sankyo Co., Ltd.); Protacyclin compounds. DE 2900352; FR 2414039; GB 2012265; JP 54095552 . |
| 【2】 Prous, J.; Castaner, J.; CS-570. Drugs Fut 1986, 11, 11, 918. |
| 中间体序号 | 中间体编号 | 品名 | CAS号 | 分子式 | 供应商 | 用于合成 |
|---|---|---|---|---|---|---|
| (XIII) | 24527 | 5(R),9-Dimethyl-1-[(2'(R),3'a(R),6'a(S))-2'-(tetrahydropyranyloxy)spiro[1,3-dioxolane-2,5'-perhydropentalen]-1-yl]deca-1(E),8-dien-3-one | C27H42O5 | 详情 | 详情 | |
| (XIV) | 24537 | 5(R),9-Dimethyl-1-[(2'(R),3'a(R),6'a(S))-2'-(tetrahydropyranyloxy)spiro[1,3-dioxolane-2,5'-perhydropentalen]-1-yl]deca-1(E),8-dien-3(S)-ol | C27H44O5 | 详情 | 详情 | |
| (XV) | 24528 | (3aS,4S,5R,6aR)-5-hydroxy-4-[(1E,3S,5R)-3-hydroxy-5,9-dimethyl-1,8-decadienyl]hexahydro-2(1H)-pentalenone | C20H32O3 | 详情 | 详情 | |
| (XVI) | 24529 | (3aS,4S,5R,6aR)-4-[5(R),9-dimethyl-3(S)-(tetrahydropyranyloxy)deca-1(E),8-dien-1-yl]-5-(tetrahydropyranyloxy)perhydropentalen-2-one | C26H42O3 | 详情 | 详情 | |
| (XVII) | 24530 | methyl 5-(triphenylphosphoranyl)pentanoate | C24H27O2P | 详情 | 详情 | |
| (XVIII) | 24531 | methyl 4-[(3aS,4S,5R,6aS)-4-[(1E,3S,5R)-5,9-dimethyl-3-(tetrahydro-2H-pyran-2-yloxy)-1,8-decadienyl]-5-(tetrahydro-2H-pyran-2-yloxy)hexahydro-2(1H)-pentalenylidene]butanoate | C35H56O6 | 详情 | 详情 | |
| (XIX) | 24532 | methyl 4-[(3aS,4S,5R,6aS)-5-hydroxy-4-[(1E,3S,5R)-3-hydroxy-5,9-dimethyl-1,8-decadienyl]hexahydro-2(1H)-pentalenylidene]butanoate | C25H40O4 | 详情 | 详情 |