Studies on anabolic steroids. 9. Tertiary sulfates of anabolic 17 alpha-methyl steroids: synthesis and rearrangement.
A simple and convenient method has been developed to prepare sulfates of anabolic 17 beta-hydroxy-17 alpha-methyl steroids. The sulfates of methandienone, 17 alpha-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.
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Institut National de la Recherche Scientifique, INRS-Santé, Université du Québec, Pointe-Claire, Canada.
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D045930:Anabolic Agents / Q000737:chemistry*; D013196:Dihydrotestosterone / Q000031:analogs & derivatives / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D008696:Methandrostenolone / Q000737:chemistry; D008777:Methyltestosterone / Q000737:chemistry; D015394:Molecular Structure; D010074:Oxandrolone / Q000737:chemistry; D013197:Stanozolol / Q000737:chemistry; D013431:Sulfates / Q000138:chemical synthesis / Q000737:chemistry*
D045930:Anabolic Agents; D013431:Sulfates; D013196:Dihydrotestosterone; D013197:Stanozolol; D010074:Oxandrolone; D008696:Methandrostenolone; C008376:mestanolone; D008777:Methyltestosterone