(Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}-5-heptenoic acid -Drug Synthesis Database

【结构式】

【分子编号】59565

【品名】(Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}-5-heptenoic acid

【CA登记号】

【分子式】C₂₃H₃₄O₅

【分子量】390.51996

【元素组成】C 70.74% H 8.78% O 20.48%

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：(XVI)

Wittig condensation of lactol (XIII) with (carboxybutyl)triphenylphosphonium bromide (XV) in the presence of potassium tert-butoxide produced the Z-olefin (XVI). Conversion of carboxylic acid (XVI) to the title isopropyl ester was then accomplished by alkylation with 2-iodopropane in the presence of DBU.

参考文献中间体

合成目标

【1】 Kovács, G.; Hermecz, I.; Szabó, T.; Ivanics, J.; Ivanics, J.; Dalmadi, G.; Bahram, R. (Chinoin Pharmaceutical and Chemical Works Co., Ltd.); Chemical process. WO 9300329 .
【2】 Resul, B.; et al.; Phenyl-substituted prostaglandins: Potent and selective antiglaucoma agents. J Med Chem 1993, 36, 2, 243.

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)	59563	(3aR,4R,5R,6aS)-4-[(3R)-3-hydroxy-5-phenylpentyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol		C₁₈H₂₆O₄	详情	详情
(XV)	13616	(4-Carboxybutyl)triphenylphosphonium bromide	17814-85-6	C₂₃H₂₄BrO₂P	详情	详情
(XVI)	59565	(Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-3-hydroxy-5-phenylpentyl]cyclopentyl}-5-heptenoic acid		C₂₃H₃₄O₅	详情	详情

Extended Information