Potassium carbonate-mediated -selective anomeric -alkylation with primary electrophiles: Application to the synthesis of glycosphingolipids.

Tetrahedron Lett

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

Published: June 2023

Stereoselective construction of a variety of β-glycosides can be achieved using abundant and inexpensive KCO-mediated stereoselective anomeric O-alkylation of sugar lactols with primary electrophiles. In addition, application of this methodology to the synthesis of various azido-modified glycosphingolipids has been accomplished in good yields and excellent anomeric selectivity using sphingosine-derived primary triflate.

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http://www.ncbi.nlm.nih.gov/pmc/articles/PMC10270675PMC
http://dx.doi.org/10.1016/j.tetlet.2023.154511DOI Listing

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