Studies on anabolic steroids. 9. Tertiary sulfates of anabolic 17α-methyl steroids: synthesis and rearrangement

Article abstract of DOI:10.1016/0039-128X(92)90048-E

A simple and convenient method has been developed to prepare sulfates of anabolic 17β-hydroxy-17α-methyl steroids.The sulfates of methandienone, 17α-methyltestosterone, mestanolone, oxandrolone, and stanozolol were prepared.Different A-ring functions were not affected under the sulfation condition.The buffered hydrolyses of these sulfates provided the 17-epimers of the original steroids and 17,17-dimethyl-18-nor-13(14)-ene steroids, presumably via the 17-carbocations. Keywords: steroids, tertiary sulfates; 17α-methyl steroids; 17β-methyl steroids; 17,17-dimethyl-18-norandrost-13(14)-enes; NMR