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Communication | Special issue | Vol 80, No. 1, 2010, pp.115-123
Published online, 12th May, 2009
DOI: 10.3987/COM-09-S(S)24
■ Mild and Selective O-Glycosylations of Primary Alcohols with the Thioglucosaminide Derivative Promoted by N-Iodosuccinimide and HBF4-Adosrobed on Silica Gel

Michio Kurosu* and Kai Li

*Department of Microbiology, Immunology and Pathology, College of Veterinary Medicine and Biomedical Sciences, Colorado State University, 1682 Campus Delivery, Fort Colllins, CO 80523-1682, U.S.A.

Abstract

Selective glycosylations of primary alcohols with the thioglucosaminide 1 are achieved by using NIS and HBF4-SiO2. HBF4-SiO2 is a mild Brønsted acid which requires primary alcohols or phenols to effectively activate 1 with NIS at rt. A wide range of functional groups are tolerated under these conditions.