FeCl3-catalyzed α-glycosidation of glycosamine pentaacetates

An efficient method for the large-scale preparation of alpha-N-acetylglycosaminides, such as fluorogenic T-N-antigen probes and an alpha-GaINAc-Ser derivative, has been achieved using FeCl3-catalyzed one-step condensation between commercially available D-glycosamine pentaacetates and fluorogenic acceptors (or serine acceptor) in refluxing 1,2-dichloroethane. Experimental simplicity, high alpha-stereoselectivity, low cost, satisfactory yield, and the environmentally benign nature are major advantages of our approach. (C) 2008 Elsevier Ltd. All rights reserved.