(2R,3R)-2-[(1R,3aS,7aR)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]-3-pentanol -Drug Synthesis Database

【结构式】

【分子编号】27526

【品名】(2R,3R)-2-[(1R,3aS,7aR)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]-3-pentanol

【CA登记号】

【分子式】C₃₆H₆₆O₃Si₂

【分子量】603.08924

【元素组成】C 71.7% H 11.03% O 7.96% Si 9.31%

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：(II)

Vitamin D derivative (I) was condensed with ethyllithium al low temperature to give, after chromatographic separation of isomers, alcohol (II). Alkylation of (II) with 6-bromo-3-ethyl-3-(trimethylsilyloxy)hexane (III) and potassium tert-butoxide in the presence of a crown ether afforded ether (IV), which was then photochemically isomerized in the presence of anthracene as a sensitizer to give (V). Final deprotection of silyl groups of (V) with 5% hydrogen fluoride in ethyl acetate-acetonitrile yielded the title compound.

参考文献中间体

合成目标

【1】 Calverley, M.J.; Grue-Sorensen, G.; Binderup, E.T. (Leo Pharmaceutical Products Ltd. A/S); Novel vitamin D analogues. EP 0522013; JP 1993505613; US 5374629; WO 9115475 .

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	27521	(2R)-2-[(1R,3aS,7aR)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]propanal	C₃₄H₆₀O₃Si₂	详情	详情
(II)	27526	(2R,3R)-2-[(1R,3aS,7aR)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]-3-pentanol	C₃₆H₆₆O₃Si₂	详情	详情
(III)	14241	(5-Bromo-2,2-diethylpentyl)(trimethyl)silane	C₁₂H₂₇BrSi	详情	详情
(IV)	27527	[5-[((1R,2R)-2-[(1R,3aS,7aR)-4-[(E)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]-1-ethylpropyl)oxy]-2,2-diethylpentyl](trimethyl)silane	C₄₈H₉₂O₃Si₃	详情	详情
(V)	27528	(1R,2R)-2-[(1R,3aS,7aR)-4-[(Z)-2-((3S,5R)-3,5-bis[[tert-butyl(dimethyl)silyl]oxy]-2-methylenecyclohexylidene)ethylidene]-7a-methyloctahydro-1H-inden-1-yl]-1-ethylpropyl 4-ethyl-4-[(trimethylsilyl)methyl]hexyl ether	C₄₈H₉₂O₃Si₃	详情	详情

Extended Information