Analysis of conjugated bile acids in human biological fluids. Synthesis of hyodeoxycholic acid 3- and 6-glycosides and related compounds

DOI: 10.1248/cpb.42.1479

Source and publish data:

Chemical and Pharmaceutical Bulletin p. 1479 - 1484 (1994)

Update date:2022-08-10

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Authors:

Iida Iida

Tazawa Tazawa

Ohshima Ohshima

Niwa Niwa

Goto Goto

Nambara Nambara

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Article abstract of DOI:10.1248/cpb.42.1479

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.

Full text of DOI:10.1248/cpb.42.1479

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