Synthesis of Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl -1,1-Dimethylpropargyl Carbamate Donors.

J Org Chem

Department of Chemistry and Biochemistry and School of Green Chemistry and Engineering, The University of Toledo, 2801 W. Bancroft Street, Toledo, Ohio 43606, United States.

Published: September 2024


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Article Abstract

Synthesis of an antigenic tetrasaccharide repeating unit of the -polysaccharide of lipopolysaccharide has been accomplished. Those four monosaccharides were assembled stereoselectively by employing our recently developed cationic gold(I)-catalyzed glycosylation methodology involving various glycosyl -1,1-dimethylpropargyl carbamate donors. The newly formed α-anomeric stereochemical configuration was controlled by the axial C2-OBz of the glycosyl donors via anchimeric assistance.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC11384238PMC
http://dx.doi.org/10.1021/acs.joc.4c01484DOI Listing

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