Synthesis of some biologically relevant beta-C-glycoconjugates.
[reaction: see text] An esterification-RCM approach to a variety of biologically relevant beta-C-glycoconjugates is reported herein. A range of carboxylic acids were coupled with several different olefin alcohols 1 to provide esters 3. The esters were then converted to the final ring-closed product 6 in three steps in 49-60% overall yield. The formed compounds are biologically relevant and serve as stable carbohydrate mimics of the corresponding O-glycosides.
Postema
Maarten H D
MH
Department of Chemistry, Wayne State University, Detroit, Michigan 48202, USA. mpostema@chem.wayne.edu
Piper
Jared L
JL
D004952:Esters / Q000138:chemical synthesis; D006001:Glycoconjugates / Q000138:chemical synthesis*; D006027:Glycosides / Q000138:chemical synthesis; D006031:Glycosylation; D007202:Indicators and Reagents
D004952:Esters; D006001:Glycoconjugates; D006027:Glycosides; D007202:Indicators and Reagents