　 -Drug Synthesis Database

【结构式】

【分子编号】41869

【品名】　

【CA登记号】

【分子式】C₃₃H₄₂O₄

【分子量】502.69408

【元素组成】C 78.85% H 8.42% O 12.73%

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：(XXIII)

The Wittig condensation of aldehyde (XIX) with phosphonium salt (XX) by means of KHMDS in THF/toluene gives the vinyloxirane (XXI), which is treated with diiron nonacarbonyl (XXII) in THF to yield the complex (XXIII). Oxidative decomplexation of (XXIII) with CAN in CH3CN gives the vinyl-beta-lactone (XXIV), which is treated with MCPBA and K2CO3 in CH2Cl2 to yield the epoxide (XXV). The ozonolysis of (XXV), followed by reduction with NaBH4 affords the hydroxymethyl-beta-lactone (XXVI), which is deepoxidated with SmI2 in tert-butanol/THF to provide the protected final intermediate (XXVII). Finally this compound is deprotected with TFA/CH2Cl2.

参考文献中间体

合成目标

【1】 Bates, R.W.; et al.; Total synthesis of the cholesterol biosynthesis inhibitor 1233A via a (Pi-allyl)tricarbonyliron lactone complex. J Chem Soc - Perkins Trans I 1999, 14, 1917.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(XIX)	41866	benzhydryl (2E,4E,7R)-11-[(2R,3R)-3-formyloxiranyl]-3,5,7-trimethyl-2,4-undecadienoate		C₃₀H₃₆O₄	详情	详情
(XX)	41867	(bromomethyl)(triphenyl)phosphorane	1779-49-3	C₁₉H₁₈BrP	详情	详情
(XXI)	41868	benzhydryl (2E,4E,7R)-3,5,7-trimethyl-11-[(2R,3S)-3-vinyloxiranyl]-2,4-undecadienoate		C₃₁H₃₈O₃	详情	详情
(XXIII)	41869			C₃₃H₄₂O₄	详情	详情
(XXIV)	41870	benzhydryl (2E,4E,7R)-3,5,7-trimethyl-11-[(2R,3R)-4-oxo-3-vinyloxetanyl]-2,4-undecadienoate		C₃₂H₃₈O₄	详情	详情
(XXV)	41871	benzhydryl (E)-3-(3-methyl-3-[(2R)-2-methyl-6-[(2R,3R)-4-oxo-3-vinyloxetanyl]hexyl]-2-oxiranyl)-2-butenoate		C₃₂H₃₈O₅	详情	详情
(XXVI)	41872	benzhydryl (E)-3-(3-[(2R)-6-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetanyl]-2-methylhexyl]-3-methyl-2-oxiranyl)-2-butenoate		C₃₁H₃₈O₆	详情	详情
(XXVII)	41873	benzhydryl (2E,4E,7R)-11-[(2R,3R)-3-(hydroxymethyl)-4-oxooxetanyl]-3,5,7-trimethyl-2,4-undecadienoate		C₃₁H₃₈O₅	详情	详情

Extended Information