Synthesis of biological precursors of cholic acid II.
This paper describes the partial syntheses of 3 alpha, 7 alpha, 12 alpha-trihydroxy-5 beta-cholestan-26-al, 7 alpha, 12 alpha, 26-trihydroxy-5 beta-cholestan-3-one and 7 alpha, 12 alpha-dihydroxy-3-oxo-5 beta-cholestan-26-al via Ag2CO3/Celite oxidation of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 26-tetrol. These bile alcohols were resolved by analytical and preparative TLC, characterized by gas-liquid chromatography and mass spectrometry. These compounds will be useful to delineate further the mechanism of oxidation of 5 beta-cholestane-3 alpha, 7 alpha, 12 alpha, 25-tetrol on the pathway to cholic acid.
D002777:Cholestanols / Q000138:chemical synthesis*; D002778:Cholestanones / Q000138:chemical synthesis; D002793:Cholic Acids / Q000096:biosynthesis*; D002849:Chromatography, Gas; D002855:Chromatography, Thin Layer; D013058:Mass Spectrometry; D008722:Methods; D013329:Structure-Activity Relationship
D002777:Cholestanols; D002778:Cholestanones; D002793:Cholic Acids; C029097:3,7,12-trihydroxycholestan-26-al; C029098:7 alpha,12 alpha,26-trihydroxy-5 beta-cholestan-3-one; C029099:7 alpha,12 alpha-dihydroxy-3-oxo-5 beta-cholestan-26-al