Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Analysis of Conjugated Bile Acids in Human Biological Fluids. Synthesis of Hyodeoxycholic Acid 3- and 6-Glycosides and Related Compounds
Takashi IIDAShinnosuke TAZAWAYukari OHSHIMAToshifumi NIWAJunichi GOTOToshio NAMBARA
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JOURNAL FREE ACCESS

1994 Volume 42 Issue 7 Pages 1479-1484

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Abstract

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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© The Pharmaceutical Society of Japan
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