• English
  • 简体中文
Login Register
Current Location: Home > Feedback Help Print

【结 构 式】

【分子编号】57938

【品名】1-[tert-butyl(dimethyl)silyl] 8-isopropyl (3S)-3-{[(1S,3S)-3-hydroxy-1-methylbutyl]oxy}octanedioate

【CA登记号】

【 分 子 式 】C22H44O6Si

【 分 子 量 】432.67326

【元素组成】C 61.07% H 10.25% O 22.19% Si 6.49%

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:(VI)

Aldehyde (II), prepared by ozonolysis of cyclohexene (I), was ketalized with (S,S)-2,4-pentanediol (III) to afford dioxane (IV). Titanium chloride-mediated coupling of acetal (IV) with the ketene acetal (V) afforded diastereoselectively adduct (VI), which was subsequently hydrolyzed to carboxylic acid (VII) by means of trifluoroacetic acid. Removal of the pentanediol moiety to furnish the (R)-alcohol (IX) was accomplished via Jones oxidation of the secondary alcohol (VII) to ketone (VIII), followed by beta-elimination in the presence of piperidinium acetate. Reduction of the free carboxyl group by borane-tetrahydrofuran complex gave diol (X), which was further converted to dimesylate (XI). Disulfide displacement of the mesylate groups provided (+)-lipoic acid isopropyl ester (XII), which was finally hydrolyzed to the title acid using K2CO3 in MeOH/H2O.

1 Elliott, J.D.; et al.; Asymmetric synthesis via acetal templates. 12. Highly diastereoselective coupling reactions with a ketene acetal. An efficient, asymmetric synthesis of R-(+)-alpha-lipoic acid. Tetrahedron Lett 1985, 26, 21, 2535.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 40446 1-cyclohexene 110-83-8 C6H10 详情 详情
(II) 57934 isopropyl 6-oxohexanoate C9H16O3 详情 详情
(III) 57935 (2S,4S)-2,4-pentanediol C5H12O2 详情 详情
(IV) 57936 isopropyl 5-[(4S,6S)-4,6-dimethyl-1,3-dioxan-2-yl]pentanoate C14H26O4 详情 详情
(V) 57937 {[1-(tert-butoxy)vinyl]oxy}(tert-butyl)dimethylsilane; 1-(tert-butoxy)vinyl tert-butyl(dimethyl)silyl ether C12H26O2Si 详情 详情
(VI) 57938 1-[tert-butyl(dimethyl)silyl] 8-isopropyl (3S)-3-{[(1S,3S)-3-hydroxy-1-methylbutyl]oxy}octanedioate C22H44O6Si 详情 详情
(VII) 57939 (3S)-3-{[(1S,3S)-3-hydroxy-1-methylbutyl]oxy}-8-isopropoxy-8-oxooctanoic acid C16H30O6 详情 详情
(VIII) 57940 (3S)-8-isopropoxy-3-{[(1S)-1-methyl-3-oxobutyl]oxy}-8-oxooctanoic acid C16H28O6 详情 详情
(IX) 57941 (3S)-3-hydroxy-8-isopropoxy-8-oxooctanoic acid C11H20O5 详情 详情
(X) 57942 isopropyl (6S)-6,8-dihydroxyoctanoate C11H22O4 详情 详情
(XI) 57943 isopropyl (6S)-6,8-bis[(methylsulfonyl)oxy]octanoate C13H26O8S2 详情 详情
(XII) 57944 isopropyl 5-[(3R)-1,2-dithiolan-3-yl]pentanoate C11H20O2S2 详情 详情
Extended Information