title: Steroid-hindered 17 beta-tertiary alcohol: characterization of dehydrated compounds.
abstract: Five dehydrated compounds obtained from a tert-butyldimethylsilylchloride/imidazole or an aqueous hydrochloric acid treatment of 17 alpha-butyl-3-O-methyl estradiol in refluxing solvent were purified and characterized. Three compounds were obtained from a direct vicinal proton elimination, the two others from a vicinal elimination after migration of methyl-18. Depending on the treatment, the proportions of dehydrated compounds are different. In addition, a general profile of experimental conditions providing a similar mixture of dehydrated compounds was also established for this steroid-hindered 17 beta-tertiary alcohol.
authors.affiliation: Medicinal Chemistry Division, CHUL Research Center, Ste-Foy, Quebec, Canada.
authors.forename: P
authors.initials: P
authors.lastname: Bydal
authors.forename: K M
authors.initials: KM
authors.lastname: Sam
authors.forename: D
authors.initials: D
authors.lastname: Poirier
mesh_terms: D002851:Chromatography, High Pressure Liquid; D004126:Dimethylformamide / Q000737:chemistry; D004958:Estradiol / Q000031:analogs & derivatives / Q000737:chemistry*; D004965:Estrogen Antagonists / Q000737:chemistry*; D006851:Hydrochloric Acid / Q000737:chemistry; D007093:Imidazoles / Q000737:chemistry; D014867:Water
chemical_list: D004965:Estrogen Antagonists; D007093:Imidazoles; D014867:Water; D004958:Estradiol; C063145:N-tert-butyldimethylsilylimidazole; C029899:imidazole; D004126:Dimethylformamide; D006851:Hydrochloric Acid