title: Studies on anabolic steroids. 9. Tertiary sulfates of anabolic 17 alpha-methyl steroids: synthesis and rearrangement.
abstract: 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.
authors.affiliation: Institut National de la Recherche Scientifique, INRS-Santé, Université du Québec, Pointe-Claire, Canada.
authors.forename: H
authors.initials: H
authors.lastname: Bi
authors.forename: R
authors.initials: R
authors.lastname: Massé
authors.forename: G
authors.initials: G
authors.lastname: Just
mesh_terms: 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*
chemical_list: D045930:Anabolic Agents; D013431:Sulfates; D013196:Dihydrotestosterone; D013197:Stanozolol; D010074:Oxandrolone; D008696:Methandrostenolone; C008376:mestanolone; D008777:Methyltestosterone