(3aR,4R,5R,6aS)-4-[(3R)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pentyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol -Drug Synthesis Database

【结构式】

【分子编号】59569

【品名】(3aR,4R,5R,6aS)-4-[(3R)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pentyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol

【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：(XX)

A closely related strategy using tetrahydropyranyl protection has been reported. Protection of the allylic alcohol (X) with dihydropyran in the presence of p-toluenesulfonic acid yielded the tetrahydropyranyl ether (XVII). Catalytic hydrogenation of (XVII) gave rise to (XVIII), which was further reduced to lactol (XIX) employing DIBAL in cold toluene. After methanolysis of the phenylbenzoyl group of (XIX), the resultant lactol (XX) was subjected to Wittig condensation with the phosphonium reagent (XV), yielding olefin (XXI). After conversion of acid (XXI) to the corresponding isopropyl ester(XXII), the tetrahydropyranyl group was removed by means of pyridinium tosylate in MeOH.

参考文献中间体

合成目标

【1】 Gutman, A.; Nisnevich, G.; Etinger, M.; Zaltzman, I.; Judovich, L.; Pertsikov, B.; A new process for the preparation of latanoprost. WO 0155101 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(X)	43182	(3aR,4R,5R,6aS)-4-[(E,3S)-3-hydroxy-5-phenyl-1-pentenyl]-2-oxohexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate		C₃₁H₃₀O₅	详情	详情
(XV)	13616	(4-Carboxybutyl)triphenylphosphonium bromide	17814-85-6	C₂₃H₂₄BrO₂P	详情	详情
(XVII)	59566	(3aR,4R,5R,6aS)-2-oxo-4-[(E,3S)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)-1-pentenyl]hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate		C₃₆H₃₈O₆	详情	详情
(XVIII)	59567	(3aR,4R,5R,6aS)-2-oxo-4-[(3R)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pentyl]hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate		C₃₆H₄₀O₆	详情	详情
(XIX)	59568	(3aR,4R,5R,6aS)-2-hydroxy-4-[(3R)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pentyl]hexahydro-2H-cyclopenta[b]furan-5-yl [1,1'-biphenyl]-4-carboxylate		C₃₆H₄₂O₆	详情	详情
(XX)	59569	(3aR,4R,5R,6aS)-4-[(3R)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pentyl]hexahydro-2H-cyclopenta[b]furan-2,5-diol		C₂₃H₃₄O₅	详情	详情
(XXI)	59570	(Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pentyl]cyclopentyl}-5-heptenoic acid		C₂₈H₄₂O₆	详情	详情
(XXII)	59571	isopropyl (Z)-7-{(1R,2R,3R,5S)-3,5-dihydroxy-2-[(3R)-5-phenyl-3-(tetrahydro-2H-pyran-2-yloxy)pentyl]cyclopentyl}-5-heptenoate		C₃₁H₄₈O₆	详情	详情

Extended Information