Improved synthesis of 5 beta-cholestan-26-oic acids.
An improved method for the synthesis of 3 alpha, 7 alpha-dihydroxy-5 beta-cholestan-26-oic acid and 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-oic acid is described. The method involves an Arndt-Eistert rearrangement of the corresponding diazoketone obtained by the action of diazoethane on 3 alpha, 7 alpha-diformyloxy-5 beta-cholane-24-carboxylic or 3 alpha, 7 alpha, 12 alpha-triformyloxy-5 beta-cholane-24-carboxylic acid chloride. The products are obtained in good yield and no isomeric 27-nor- 24-methyl acid contaminants are formed as encountered in the commonly employed Kolbe synthesis.
D001647:Bile Acids and Salts / Q000138:chemical synthesis*; D002777:Cholestanols / Q000138:chemical synthesis*; D002849:Chromatography, Gas; D013058:Mass Spectrometry; D008722:Methods; D009904:Optical Rotation; D013055:Spectrophotometry, Infrared
D001647:Bile Acids and Salts; D002777:Cholestanols