Facile Approach to 2-Acetamido-2-deoxy-β-d-Glucopyranosides via a Furanosyl Oxazoline

A concise and convenient route that may be easily scaled is reported for the preparation of unprotected beta-glucopyranosides of N-acetyl-D-glucosamine. Reaction of a wide variety of alcohols with a reactive, readily prepared furanosyl oxazoline under acidic conditions affords the corresponding beta-D-glucopyranosides in good to high yields. Primary alcohols gave only beta-D-glucopyranosides. A mechanism is proposed for this transformation. [reaction: see text]