Title

Synthesis of anomerically pure, furanose-free benzyl-2-amino-2-deoxy-mannuronic acid derivatives

Document Type

Article

Publication Title

Synthetic Communications

Department

Chemistry

ISSN

0039-7911

Volume

37

Issue

14

DOI

10.1080/00397910701410871

First Page

2355

Last Page

2381

Publication Date

1-1-2007

Abstract

The anomerically pure benzyl α-d-glycoside of 2-amino-2-deoxy-mannopyranoside was synthesized from d-glucopyranose via 2-amino-2-deoxy-d-altrose intermediates. Unlike the direct synthesis from mannosamine in the literature, our method provides furanose-free products. A new method for the preparation of cis-2,3-oxazolidinones of 2-amino-2-deoxy-sugars was developed. A selective removal of the glycosidic benzyl group in the presence of 4,6-O-benzylidene protection was developed, which may provide new routes for the synthesis of oligosaccharides. Furanose-free derivatives of α-benzyl-2-amino-2-deoxy-mannopyranuronic acids synthesized here offered possibilities for direct comparisons to prior literature preparations.