Towards oligosaccharide libraries: A study of the random galactosylation of unprotected N-acetylglucosamine

Article abstract of DOI:10.1016/0968-0896(96)00064-8

A single reaction of an unprotected β-D-GlcNAc glycoside with tetra-O-acetyl-α-D-galactopyranosyl trichloroacetimidate in dioxane, catalyzed by BF₃-etherate, was shown to yield all six possible Gal-GlcNAc disaccharides. This result is surprising not only because significant amounts of cc-linked disaccharides were formed, despite the presence of a participating group at O-2 of the glycosyl donor, but also because glycosylation of the primary OH-6 is not the dominant reaction. These results suggest 'random-glycosylation' to be a valid strategy for the rapid production of oligosaccharide libraries.