Facile approach to 2-acetamido-2-deoxy-beta-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]
Cai
Ye
Y
Alberta Ingenuity Center for Carbohydrate Science, Department of Chemistry, University of Alberta, Edmonton, Alberta T6G 2G2, Canada.
Ling
Chang-Chun
CC
Bundle
David R
DR
D020650:Combinatorial Chemistry Techniques; D005944:Glucosamine / Q000031:analogs & derivatives* / Q000737:chemistry*; D005960:Glucosides / Q000138:chemical synthesis* / Q000737:chemistry*; D006031:Glycosylation; D015394:Molecular Structure; D010080:Oxazoles / Q000737:chemistry; D013237:Stereoisomerism
D005960:Glucosides; D010080:Oxazoles; D005944:Glucosamine