Alfaprostol, Ro-229000, K-11941, Alfavet, -Drug Synthesis Database

【结构式】

【药物名称】Alfaprostol, Ro-229000, K-11941, Alfavet

【化学名称】[1R-[1alpha(Z),2beta(S*),3alpha,5alpha]]-7-[2-(5-Cyclohexyl-3-hydroxy-1-pentynyl)-3,5-dihydroxycyclopentyl]-5-heptenoic acid methyl ester
　　　　　　7-[(1R,2S,3R,5S)-2-[5-Cyclohexyl-3(S)-hydroxy-1-pentynyl]-3,5-dihydroxycyclopentyl]-5(Z)-heptenoic acid methyl ester
　　　　　　18,19,20-Trinor-17-cyclohexyl-13,14-didehydro-PGF2alpha methyl ester
　　　　　　18,19,20-Trinor-17-cyclohexyl-9,11,15-trihydroxyprosta-5-en-13-inoic acid methyl ester

【CA登记号】74176-31-1

【分子式】C₂₄H₃₈O₅

【分子量】406.56746

【开发单位】Pfizer (Originator), Roche (Originator)

【药理作用】GnRH (LHRH) Antagonists

合成路线1

The Wittig condensation of the bicyclic lactol (I) with 4-(methoxycarbonyl)butyl triphenylphosphonium bromide (II) by means of sodium methylsulfinyl carbanide in DMSO and simultaneous dehydrobromination gives the bis(tetrahydropyranyl) derivative (III), which is finally deprotected by a treatment with oxalic acid in refluxing acetone.

参考文献中间体

【1】 Gandolfi, C.; Pellegata, R.; Ceserani, R.; Usardi, M.M. (Pharmacia Corp.); Omega-nor-cycloalkyl-13,14-dehydroprostaglandins. DE 2539116; FR 2285866; FR 2378757; GB 1483880; JP 51125044; JP 58135858; US 4035415; US 4361577 .
【2】 Castaner, J.; Serradell, M.N.; de Angelis, L.; Alfaprostol. Drugs Fut 1985, 10, 1, 9.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	29030	(4S,5R)-4-[(Z,3R)-2-bromo-5-cyclohexyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-pentenyl]-5-[(tetrahydro-2H-pyran-2-yloxy)methyl]hexahydro-2H-cyclopenta[b]furan-2-ol	C₃₀H₄₉BrO₆	详情	详情
(II)	26177	(5-methoxy-5-oxopentyl)(triphenyl)phosphonium bromide	C₂₄H₂₆BrO₂P	详情	详情
(III)	29031	methyl (Z)-7-[(1R,2S,3R,5S)-2-[(3S)-5-cyclohexyl-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]-1-pentynyl]-5-hydroxy-3-[(tetrahydro-2H-pyran-2-yloxy)methyl]cyclopentyl]-5-heptenoate	C₃₆H₅₈O₇	详情	详情

Extended Information