Abstract
Competitive glycosylation experiments with a galactofuranosyl trichloroacetimidate donor were performed with glucosamine acceptors having a free 4-OH group and carrying different protecting groups at N-2, O-3, and O-6. The most reactive acceptor is the N-dimethylmaleimido 3,6-di-O-benzylated derivative ( 6c), which reacts even faster than the oxazolidinone 1a. Molecular orbital calculations have helped to rationalize these experimental facts in terms of a hard–hard reaction occurring between the donor and the acceptor.
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