Oxazolidinone protection of N-acetylglucosamine confers high reactivity on the 4-hydroxy group in glycosylation.
[reaction: see text] The preparation of a convenient oxazolidinone protected N-acetyl glucosamine 4-OH derivative is reported. This substance exhibits enhanced reactivity as a glycosyl acceptor in a variety of coupling methods, the products of which are converted to the target N-acetylglucosaminyl saccharides under very mild conditions.
Crich
David
D
Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Chicago, Illinois 60607-7061, USA. dcrich@uic.edu
Vinod
A U
AU
D000117:Acetylglucosamine / Q000737:chemistry*; D002236:Carbohydrate Conformation; D006031:Glycosylation; D023303:Oxazolidinones / Q000138:chemical synthesis / Q000737:chemistry*; D013329:Structure-Activity Relationship; D013865:Thioglycosides / Q000737:chemistry
D023303:Oxazolidinones; D013865:Thioglycosides; D000117:Acetylglucosamine