作者:John R. Williams、Jeffrey C. Boehm
DOI:10.1016/0039-128x(94)00066-l
日期:1995.4
The syntheses of the diacylglyceryl-sulfide 4a, sulfoxide 4b, and sulfone 4c of dehydroepiandrosterone (3 beta-hydroxyandrost-5-en-17-one, DHEA, 1a) are described. Nucleophilic substitution of 1,2-dipalmitoyl-3-iodo-rac-3-deoxyglycerol (2) with 3 beta-mercaptoandrost-5-en-17-one (3) afforded the diacylglyceryl-sulfide (4). Selective oxidation of 4 with m-chloroperbenzoic acid gave the diacylglyceryl-sulfoxide
描述了脱氢表雄酮的二酰基甘油硫醚4a,亚砜4b和砜4c(3β-羟基雄酮-5-en-17-one,DHEA,1a)的合成。用3个β-巯基和5--5-en-17-一(3)亲核取代1,2-二棕榈酰基-3-碘-rac-3-脱氧甘油(2),得到二酰基甘油硫醚(4)。用间氯过苯甲酸选择性氧化4得到DHEA的二酰基甘油基亚砜4b和二酰基甘油基砜4c。硫化物4a是6磷酸葡萄糖脱氢酶的极弱抑制剂,而砜4c不抑制该酶。