Analysis of conjugated bile acids in human biological fluids. Synthesis of hyodeoxycholic acid 3- and 6-glycosides and related compounds.
The glucuronide, glucoside and N-acetylglucosaminide conjugates of hyodeoxycholic 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 reaction 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 glycoside methyl ester-acetates with tert-butylamine-borane complex, and 3) subsequent hydrolysis with aqueous lithium hydroxide.
Iida
T
T
College of Engineering, Nihon University, Fukushima, Japan.
Tazawa
S
S
Ohshima
Y
Y
Niwa
T
T
Goto
J
J
Nambara
T
T
D001647:Bile Acids and Salts / Q000032:analysis / Q000138:chemical synthesis*; D003840:Deoxycholic Acid / Q000032:analysis / Q000138:chemical synthesis*; D006027:Glycosides / Q000032:analysis / Q000138:chemical synthesis*; D006801:Humans; D007536:Isomerism
D001647:Bile Acids and Salts; D006027:Glycosides; D003840:Deoxycholic Acid; C010471:hyodeoxycholic acid