Reverse cross-coupling in the synthesis 3 alpha, 7 alpha-dihydroxy-5 beta-cholestanoic acid.
The present report describes the characterization of (24R and 24S)-27-nor-24-methyl-3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acids obtained in considerable amounts during the synthesis of (25RS)-3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acid by the electrolytic coupling of chenodeoxycholic acid and the half ester of methylsuccinic acid. The mixture of 24R and 24S diastereomers was resolved by analytical and preparative thin-layer chromatography and characterized by gas-liquid chromatography, proton magnetic resonance, and molecular rotation differences. For reference, the model compound, 27-nor-3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acid, was synthesized by electrolytic coupling of chenodeoxycholic acid and the half ester of succinic acid.
D002777:Cholestanols / Q000138:chemical synthesis*; D002849:Chromatography, Gas; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008722:Methods; D008968:Molecular Conformation; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared; D013329:Structure-Activity Relationship
D002777:Cholestanols