(2S)-5-(benzyloxy)-2-methylpentanal -Drug Synthesis Database

【结构式】

【分子编号】47092

【品名】(2S)-5-(benzyloxy)-2-methylpentanal

【CA登记号】

【分子式】C₁₃H₁₈O₂

【分子量】206.28472

【元素组成】C 75.69% H 8.8% O 15.51%

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：(I)

The intermediate olefin (XI) was prepared as follows. The diastereoselective aldol condensation between aldehyde (I) and ketone (II) provided the desired aldol diastereoisomer (III). Acetonide hydrolysis in (III) by means of pyridinium tosylate in MeOH, followed by protection of the resultant triol with tert-butyl-dimethylsilyl triflate, gave the tris-silyl ether (IV). The primary hydroxyl group of (IV) was then selectively deprotected by treatment with camphorsulfonic acid, yielding alcohol (V). Swern oxidation of (V) produced aldehyde (VI), which was further oxidized to carboxylic acid (VII) by means of sodium chlorite.

参考文献中间体

合成目标

【1】 Altmann, K.-H.; et al.; Synthesis and biological evaluation of highly potent analogues of epothilones B and D. Bioorg Med Chem Lett 2000, 10, 24, 2765.

中间体序号	中间体编号	品名	分子式	供应商	用于合成
(I)	47092	(2S)-5-(benzyloxy)-2-methylpentanal	C₁₃H₁₈O₂	详情	详情
(II)	27176	2-[(4S)-2,2-dimethyl-1,3-dioxan-4-yl]-2-methyl-3-pentanone	C₁₂H₂₂O₃	详情	详情
(III)	47093	(4R,5S,6S)-9-(benzyloxy)-2-[(4S)-2,2-dimethyl-1,3-dioxan-4-yl]-5-hydroxy-2,4,6-trimethyl-3-nonanone	C₂₅H₄₀O₅	详情	详情
(IV)	47094	(5S,6R,9S)-5-[(1S)-4-(benzyloxy)-1-methylbutyl]-9-[[tert-butyl(dimethyl)silyl]oxy]-2,2,3,3,6,8,8,13,13,14,14-undecamethyl-4,12-dioxa-3,13-disilapentadecan-7-one	C₄₀H₇₈O₅Si₃	详情	详情
(V)	47095	(5S,8R,9S)-9-[(1S)-4-(benzyloxy)-1-methylbutyl]-5-(2-hydroxyethyl)-2,2,3,3,6,6,8,11,11,12,12-undecamethyl-4,10-dioxa-3,11-disilatridecan-7-one	C₃₄H₆₄O₅Si₂	详情	详情
(VI)	47096	(3S,6R,7S,8S)-11-(benzyloxy)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8-tetramethyl-5-oxoundecanal	C₃₄H₆₂O₅Si₂	详情	详情
(VII)	47097	(3S,6R,7S,8S)-11-(benzyloxy)-3,7-bis[[tert-butyl(dimethyl)silyl]oxy]-4,4,6,8-tetramethyl-5-oxoundecanoic acid	C₃₄H₆₂O₆Si₂	详情	详情

Extended Information