(7R,10S)-7-isopropyl-10-methyl-1,5-dithiaspiro[5.5]undecane -Drug Synthesis Database

【结构式】

【分子编号】57961

【品名】(7R,10S)-7-isopropyl-10-methyl-1,5-dithiaspiro[5.5]undecane

【CA登记号】

【分子式】C₁₃H₂₄S₂

【分子量】244.46556

【元素组成】C 63.87% H 9.9% S 26.23%

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：(XXXIII)

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.

参考文献中间体

合成目标

【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