A STEREOSELECTIVE α-GLUCOSYLATION BY USE OF A MIXTURE OF 4-NITROBENZENESULFONYL CHLORIDE, SILVER TRIFLUOROMETHANESULFONATE, N,N-DIMETHYLACETAMIDE, AND TRIETHYLAMINE

Article abstract of DOI:10.1016/0008-6215(84)85271-4

Stereoselective α-glucosylation of partially protected carbohydrates with 2,3,4,6-tetra-O-benzyl-α-D-glucopyranose in dichloromethane, in the presence of a quaternary mixture of 4-nitrobenzenesulfonyl chloride, silver trifluoromethanesulfonate, N,N-dimethylacetamide, and triethylamine gave O-α-D-glucopyranosyl-(1->4)- and -(1->6)-2-acetamido-2-deoxy-D-glucopyranose (N-acetylmaltosamine and N-acetylisomaltosamine).A step-by-step synthesis of O-α-D-glucopyranosyl-(1->4)-O-<α-D-glucopyranosyl-(1->6)>-D-glucopyranose is described.