Chemical and Pharmaceutical Bulletin p. 1479 - 1484 (1994)
Update date:2022-08-10
Topics:
Iida
Tazawa
Ohshima
Niwa
Goto
Nambara
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-6α-hydroxy and 6-oxo-3α-hydroxy esters with an appropriate α- 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.
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