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【结 构 式】

【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%

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:(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
Extended Information