(Z)-7-((1S,2R,3R,5S)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)-2-[2-(tetrahydro-2H-pyran-2-yloxy)-4-[3-(trifluoromethyl)phenyl]butoxy]cyclopentyl)-5-heptenoic acid -Drug Synthesis Database

【结构式】

【分子编号】50706

【品名】(Z)-7-((1S,2R,3R,5S)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)-2-[2-(tetrahydro-2H-pyran-2-yloxy)-4-[3-(trifluoromethyl)phenyl]butoxy]cyclopentyl)-5-heptenoic acid

【CA登记号】

【分子式】C₃₃H₄₇F₃O₈

【分子量】628.7265896

【元素组成】C 63.04% H 7.53% F 9.07% O 20.36%

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)

Wittig reaction of lactol (XIII) with the ylide generated from phosphonium salt (XIV) and potassium tert-butoxide afforded acid (XV), which was subsequently esterified with isopropyl iodide and DBU to give the isopropyl ester (XVI). Cleavage of the tetrahydropyranyl ethers of (XVI) under mildly acidic conditions followed by HPLC separation using a chiral column provided the desired alcohol diastereoisomer (XVII). Finally, hydrolysis of ester (XVII) under basic conditions provided the corresponding free acid.

参考文献中间体

合成目标

【1】 Feng, Z.; et al.; Design and synthesis of 13-oxa prostaglandin analogs as antiglaucoma agents. 222nd ACS Natl Meet (Aug 26 2001, Chicago) 2001, Abst MEDI 236.
【2】 Feng, Z.; Hellberg, M.R. (Alcon Laboratories, Inc.); 13-Oxa prostaglandins for the treatment of glaucoma and ocular hypertension. US 6232344; WO 9932441 .

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)	50705	(3aR,4R,5R,6aS)-5-(tetrahydro-2H-pyran-2-yloxy)-4-[2-(tetrahydro-2H-pyran-2-yloxy)-4-[3-(trifluoromethyl)phenyl]butoxy]hexahydro-2H-cyclopenta[b]furan-2-ol		C₂₈H₃₉F₃O₇	详情	详情
(XIV)	13616	(4-Carboxybutyl)triphenylphosphonium bromide	17814-85-6	C₂₃H₂₄BrO₂P	详情	详情
(XV)	50706	(Z)-7-((1S,2R,3R,5S)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)-2-[2-(tetrahydro-2H-pyran-2-yloxy)-4-[3-(trifluoromethyl)phenyl]butoxy]cyclopentyl)-5-heptenoic acid		C₃₃H₄₇F₃O₈	详情	详情
(XVI)	50707	isopropyl (Z)-7-((1S,2R,3R,5S)-5-hydroxy-3-(tetrahydro-2H-pyran-2-yloxy)-2-[2-(tetrahydro-2H-pyran-2-yloxy)-4-[3-(trifluoromethyl)phenyl]butoxy]cyclopentyl)-5-heptenoate		C₃₆H₅₃F₃O₈	详情	详情
(XVII)	50708	isopropyl (Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-([(2S)-2-hydroxy-4-[3-(trifluoromethyl)phenyl]butyl]oxy)cyclopentyl]-5-heptenoate		C₂₆H₃₇F₃O₆	详情	详情

Extended Information