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【结 构 式】

【分子编号】57962

【品名】(6S,7R,10S)-7-isopropyl-10-methyl-5-thia-1-thioniaspiro[5.5]undecan-1-olate

【CA登记号】

【 分 子 式 】C13H24OS2

【 分 子 量 】260.46496

【元素组成】C 59.95% H 9.29% O 6.14% S 24.62%

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:(XXXIV)

A short synthetic strategy utilized the cyclic thioketal (XXXIII), derived from d-menthone (XXXII) and 1,3-propanedithiol, as the chiral template. Stereospecific oxidation of dithiane (XXXIII) employing NaIO4 produced sulfoxide (XXXIV). The carbanion generated from sulfoxide (XXXIV) was stereoselectively alkylated by 5-bromopentanoic acid (XXXV) in the presence of TMEDA to furnish the trans alkylated compound (XXXVI). Finally, acidic hydrolysis of (XXXVI) formed the intermediate mercapto sulfinic acid (XXXVII) which spontaneously cyclized to the desired dithiolane derivative.

1 Menon, R.B.; et al.; Stereospecific synthesis of alpha-lipoic acid. Tetrahedron Lett 1987, 28, 44, 5313.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(XXXII) 10208 L-Menthone; (2S,5R)-2-Isopropyl-5-methylcyclohexanone 14073-97-3 C10H18O 详情 详情
(XXXIII) 57961 (7R,10S)-7-isopropyl-10-methyl-1,5-dithiaspiro[5.5]undecane C13H24S2 详情 详情
(XXXIV) 57962 (6S,7R,10S)-7-isopropyl-10-methyl-5-thia-1-thioniaspiro[5.5]undecan-1-olate C13H24OS2 详情 详情
(XXXV) 57963 5-Bromo-n-valeric acid; 5-Bromopentanoic acid; 5-Bromovaleric acid 2067-33-6 C5H9BrO2 详情 详情
(XXXVI) 57964 (2R,6S,7R,10S)-2-(4-carboxybutyl)-7-isopropyl-10-methyl-5-thia-1-thioniaspiro[5.5]undecan-1-olate C18H32O3S2 详情 详情
(XXXVII) 57965 (6R)-6-(hydroxysulfanyl)-8-sulfanyloctanoic acid C8H16O3S2 详情 详情
Extended Information