ANALYSIS OF CONJUGATED BILE-ACIDS IN HUMAN BIOLOGICAL-FLUIDS - SYNTHESIS OF HYODEOXYCHOLIC ACID 3-GLYCOSIDE AND 6-GLYCOSIDE AND RELATED-COMPOUNDS

The glucuronide, glucoside and N-acetylglucosaminide conjugates of hyo deoxycholic acid were synthesized. In addition, murideoxycholic acid 3 -glycosides and some of their C-5 epimeric analogs were also prepared. The principal reactions used are 1) the Koenigs-Knorr condensation re action of 3-oxo-6 alpha-hydroxy and 6-oxo-3 alpha-hydroxy esters with an appropriate alpha-acetohalosugar catalyzed by cadmium carbonate in benzene under reflux, 2) reduction of the resulting bile acid glycosid e methyl ester-acetates with tert-butylamine-borane complex, and 3) su bsequent hydrolysis with aqueous lithium hydroxide.