【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% |
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 |