Synthesis of some diol DErivatives as potential reagents in steroid chemistry

Abstract

The multistage syntheses of the p-toluenesulphonyloxy esters (1-benzyloxy-4-p-toluenesulphonyloxybutane (3a) 1-benzyloxy-6-p-toluenesulphonyloxyhexane (3b) and 1-benzyloxy-10-p-toluenesulphonyloxydecane (3c)(, alkyl chlorides (1-benzyloxy-4-chlorobutane (4a), 1-benzyloxy-6-chlorohexane (4b) and 1-benzyloxy-10-chlorodecane (4c)(, as well as alkyl iodides (1-benzyloxy-4-iodobutane (5a), 1-benzyloxy-6-iodohexane (5b) and 1-benzyloxy-10-iododecane (5c)( with the terminal O-benzyl groups starting from 1,4-butanediol (1a), 1,6-hexanediol (1b) and 1,10-decanediol (1c) were carried out. The possibilities of formation and addition of the corresponding Grignard reagent to the C-17 carbonyl group of dehydroepiandrosterone were investigated.