2-[(3S,4R,5R)-3,5-bis{[tert-butyl(diphenyl)silyl]oxy}-4-(3-{[tert-butyl(diphenyl)silyl]oxy}propoxy)-2-methylenecyclohexylidene]-1-ethanol -Drug Synthesis Database

【结构式】

【分子编号】59887

【品名】2-[(3S,4R,5R)-3,5-bis{[tert-butyl(diphenyl)silyl]oxy}-4-(3-{[tert-butyl(diphenyl)silyl]oxy}propoxy)-2-methylenecyclohexylidene]-1-ethanol

【CA登记号】

【分子式】C₆₀H₇₄O₅Si₃

【分子量】959.50106

【元素组成】C 75.11% H 7.77% O 8.34% Si 8.78%

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：(XLIX)

Basic hydrolysis of the pivalate esters of (XLV) followed by protection with tert-butyldimethylsilyl chloride provided the trisilylated derivative (XLVI). The p-methoxybenzyl protecting group of (XLVI) was then removed by treatment with DDQ, yielding (XLVII). Red-Al reduction of the propargyl alcohol (XLVII), followed by iodination produced the vinyl iodide (XLVIII). Intramolecular cyclization of iodide (XLVIII) under Heck reaction conditions gave rise to the key allyl alcohol intermediate (XXX), along with its undesired diastereoisomer (XLIX), which was separated by column chromatography

参考文献中间体

合成目标

【1】 Hatakeyama, S.; Ikeda, T.; Maeyama, J.; Esumi, T.; Iwabuchi, Y.; Irie, H.; Convergent synthesis of 1alpha, 25-dihydroxy-2beta-(3-hydroxypropoxy)vitamin D3 (ED-71). Bioorg Med Chem Lett 1997, 7, 22, 2871.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(XXX)	59876	2-[(3R,4R,5R)-3,5-bis{[tert-butyl(diphenyl)silyl]oxy}-4-(3-{[tert-butyl(diphenyl)silyl]oxy}propoxy)-2-methylenecyclohexylidene]-1-ethanol	C₆₀H₇₄O₅Si₃	详情	详情
(XLV)	59882	3-({(1R,2R)-1-{1-[(2,2-dimethylpropanoyl)oxy]-2-propenyl}-2-hydroxy-6-[(4-methoxybenzyl)oxy]-4-hexynyl}oxy)propyl pivalate	C₃₀H₄₄O₈	详情	详情
(XLVI)	59884	(5R,6R)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-6-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-8-nonen-2-ynyl 4-methoxybenzyl ether; (6R)-6-{(1R)-1-{[tert-butyl(dimethyl)silyl]oxy}-5-[(4-methoxybenzyl)oxy]-3-pentynyl}-2,2,3,3,12,12,13,13-octamethyl-5-vinyl-4,7,11-trioxa-3,12-disilatetradecane	C₃₈H₇₀O₆Si₃	详情	详情
(XLVII)	59885	(5R,6R)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-6-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-8-nonen-2-yn-1-ol	C₃₀H₆₂O₅Si₃	详情	详情
(XLVIII)	59886	(2Z,5R,6R)-5,7-bis{[tert-butyl(dimethyl)silyl]oxy}-6-(3-{[tert-butyl(dimethyl)silyl]oxy}propoxy)-3-iodo-2,8-nonadien-1-ol	C₃₀H₆₃IO₅Si₃	详情	详情
(XLIX)	59887	2-[(3S,4R,5R)-3,5-bis{[tert-butyl(diphenyl)silyl]oxy}-4-(3-{[tert-butyl(diphenyl)silyl]oxy}propoxy)-2-methylenecyclohexylidene]-1-ethanol	C₆₀H₇₄O₅Si₃	详情	详情

Extended Information