C26-Analogs of naturally occurring C27 bile alcohols.
C26 Bile of the 24-nor-5beta-cholestane series were prepared starting from methyl cholate. A Grignard reaction of methyl magnesium iodide with methyl cholate yielded 24-nor-5beta-cholestane-3alpha, 7alpha, 12alpha, 25-tetrol which was dehydrated TO FORM a mixture of 24-nor-5beta-cholest-23-ene-3alpha, 7alpha, 12 alpha-triol and the corresponding delta25 compound. Oxidation of the former with OsO4 yielded 24-nor-5beta-cholestane-3alpha, 7alpha, 12alpha, 23epsilon, 25pentol, while catalytic hydrogenation of a mixture of the delta23 and delta25 triols resulted in the formation of 24-nor-5beta-cholestane-3-alpha-, 7alpha-12alpha-triol. The structures of these new compounds were confirmed by infrared and nuclear megnetic resonance spectrometry and by gas-liquid chromatography-mass spectrometry.
D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009654:Norsteroids / Q000138:chemical synthesis; D013055:Spectrophotometry, Infrared; D013261:Sterols / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D009654:Norsteroids; D013261:Sterols