(2S,3R)-2-[(benzyloxy)methoxy]-3-pentanol -Drug Synthesis Database

【结构式】

【分子编号】34847

【品名】(2S,3R)-2-[(benzyloxy)methoxy]-3-pentanol

【CA登记号】

【分子式】C₁₃H₂₀O₃

【分子量】224.3

【元素组成】C 69.61% H 8.99% O 21.4%

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：(XXIX)

Methyl (S)-lactate (XXVI) was protected as the benzyloxymethyl ether (XXVII) and subsequently reduced to aldehyde (XXVIII) with DIBAL in toluene at -78 C. Addition of ethylmagnesium bromide to this aldehyde (XXVIII) produced a diastereomeric mixture of carbinols. The required (2S,3R) isomer (XXIX) was isolated by column chromatography and then converted to brosylate ester (XXX) by reaction with 4-bromobenzenesulfonyl chloride. Nucleophilic displacement of the brosylate group of (XXX) by triazolone (XXV) produced the N-alkylated triazolone (XXXI). Then, acid cleavage of the benzyloxymethyl protec-ting group of (XXXI) provided alcohol (XXXII).

参考文献中间体

合成目标

【1】 Saksena, A.K.; Girijavallabhan, V.M.; Lovey, R.G.; Pike, R.E.; Wang, H.; Liu, Y.-T.; Ganguly, A.K.; Bennett, F. (Schering Corp.); Tetrahydrofuran antifungals. EP 0773941; WO 9638443 .

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
	18964	4-bromobenzenesulfonyl chloride	98-58-8	C₆H₄BrClO₂S	详情	详情
(XXV)	16351	4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₃₂H₃₂F₂N₈O₃	详情	详情
(XXVI)	17075	propionic acid, 2-hydroxy-, methyl ester, (S)-; methyl (2S)-2-hydroxypropanoate	27871-49-4	C₄H₈O₃	详情	详情
(XXVII)	34845	methyl (2S)-2-[(benzyloxy)methoxy]propanoate		C₁₂H₁₆O₄	详情	详情
(XXVIII)	34846	(2S)-2-[(benzyloxy)methoxy]propanal		C₁₁H₁₄O₃	详情	详情
(XXIX)	34847	(2S,3R)-2-[(benzyloxy)methoxy]-3-pentanol		C₁₃H₂₀O₃	详情	详情
(XXX)	34848	(1R,2S)-2-[(benzyloxy)methoxy]-1-ethylpropyl 4-bromobenzenesulfonate		C₁₉H₂₃BrO₅S	详情	详情
(XXXI)	34849	2-[(1S,2S)-2-[(benzyloxy)methoxy]-1-ethylpropyl]-4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₄₅H₅₀F₂N₈O₅	详情	详情
(XXXII)	34850	4-[4-[4-(4-[[(3R,5R)-5-(2,4-difluorophenyl)-5-(1H-1,2,4-triazol-1-ylmethyl)tetrahydro-3-furanyl]methoxy]phenyl)-1-piperazinyl]phenyl]-2-[(1S,2S)-1-ethyl-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one		C₃₇H₄₂F₂N₈O₄	详情	详情

Extended Information