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Synthesis of 5 alpha-androstane-3 alpha, 16 alpha, 17 beta-triol from 3 beta-hydroxy-5-androsten-17-one. 1984

S N Newaz, and R K Tcholakian

5 alpha-Androstane-3 alpha, 16 alpha, 17 beta-triol was synthesized from 3 beta-hydroxy-5-androsten-17-one. The procedure involved catalytic hydrogenation of 3 beta-hydroxy-5-androsten-17-one to 3 beta-hydroxy-5 alpha-androstan-17-one. This was followed by conversion of the 3 beta-hydroxy group to 3 alpha-benzoyloxy group by the Mitsunobu reaction. Further treatment with isopropenyl acetate yielded 5 alpha-androsten-16-ene-3 alpha, 17-diol 3-benzoate 17-acetate. This was then converted to 3 alpha, 17-dihydroxy-5 alpha-androstan-16-one 3-benzoate 17-acetate via the unstable epoxide intermediate after treatment with m-cloroperoxybenzoic acid. LiA1H4 reduction of this compound formed 5 alpha-androstane-3 alpha, 16 alpha, 17 beta-triol. 1H and 13C NMR of various steroids are presented to confirm the structure of this compound.

UI MeSH Term Description Entries
D007202 Indicators and Reagents Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499) Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D009682 Magnetic Resonance Spectroscopy Spectroscopic method of measuring the magnetic moment of elementary particles such as atomic nuclei, protons or electrons. It is employed in clinical applications such as NMR Tomography (MAGNETIC RESONANCE IMAGING). In Vivo NMR Spectroscopy,MR Spectroscopy,Magnetic Resonance,NMR Spectroscopy,NMR Spectroscopy, In Vivo,Nuclear Magnetic Resonance,Spectroscopy, Magnetic Resonance,Spectroscopy, NMR,Spectroscopy, Nuclear Magnetic Resonance,Magnetic Resonance Spectroscopies,Magnetic Resonance, Nuclear,NMR Spectroscopies,Resonance Spectroscopy, Magnetic,Resonance, Magnetic,Resonance, Nuclear Magnetic,Spectroscopies, NMR,Spectroscopy, MR
D002621 Chemistry A basic science concerned with the composition, structure, and properties of matter; and the reactions that occur between substances and the associated energy exchange.
D002849 Chromatography, Gas Fractionation of a vaporized sample as a consequence of partition between a mobile gaseous phase and a stationary phase held in a column. Two types are gas-solid chromatography, where the fixed phase is a solid, and gas-liquid, in which the stationary phase is a nonvolatile liquid supported on an inert solid matrix. Chromatography, Gas-Liquid,Gas Chromatography,Chromatographies, Gas,Chromatographies, Gas-Liquid,Chromatography, Gas Liquid,Gas Chromatographies,Gas-Liquid Chromatographies,Gas-Liquid Chromatography
D000732 Androstanols Androstanes and androstane derivatives which are substituted in any position with one or more hydroxyl groups. Hydroxyandrostanes
D013058 Mass Spectrometry An analytical method used in determining the identity of a chemical based on its mass using mass analyzers/mass spectrometers. Mass Spectroscopy,Spectrometry, Mass,Spectroscopy, Mass,Spectrum Analysis, Mass,Analysis, Mass Spectrum,Mass Spectrum Analysis,Analyses, Mass Spectrum,Mass Spectrum Analyses,Spectrum Analyses, Mass
D015113 Androstane-3,17-diol The unspecified form of the steroid, normally a major metabolite of TESTOSTERONE with androgenic activity. It has been implicated as a regulator of gonadotropin secretion. 5 Androstane 3,17 diol,5 alpha-Androstane-3 alpha,17 beta-diol,5 alpha-Androstane-3 beta,17 alpha-diol,5 alpha-Androstane-3 beta,17 beta-diol,5 alpha-Androstane-3alpha,17 beta-diol,5 beta-Androstane-3 alpha,17 beta-diol,5-Androstane-3,17-diol,5alpha-Androstane-3beta,17alpha-diol,5 alpha Androstane 3 alpha,17 beta diol,5 alpha Androstane 3 beta,17 alpha diol,5 alpha Androstane 3 beta,17 beta diol,5 alpha Androstane 3alpha,17 beta diol,5 beta Androstane 3 alpha,17 beta diol,5alpha Androstane 3beta,17alpha diol,Androstane 3,17 diol
D055598 Chemical Phenomena The composition, structure, conformation, and properties of atoms and molecules, and their reaction and interaction processes. Chemical Concepts,Chemical Processes,Physical Chemistry Concepts,Physical Chemistry Processes,Physicochemical Concepts,Physicochemical Phenomena,Physicochemical Processes,Chemical Phenomenon,Chemical Process,Physical Chemistry Phenomena,Physical Chemistry Process,Physicochemical Phenomenon,Physicochemical Process,Chemical Concept,Chemistry Process, Physical,Chemistry Processes, Physical,Concept, Chemical,Concept, Physical Chemistry,Concept, Physicochemical,Concepts, Chemical,Concepts, Physical Chemistry,Concepts, Physicochemical,Phenomena, Chemical,Phenomena, Physical Chemistry,Phenomena, Physicochemical,Phenomenon, Chemical,Phenomenon, Physicochemical,Physical Chemistry Concept,Physicochemical Concept,Process, Chemical,Process, Physical Chemistry,Process, Physicochemical,Processes, Chemical,Processes, Physical Chemistry,Processes, Physicochemical

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