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

Authors

Tony M. K. Chiu, University of the PacificFollow
Katina Sigillo, University of the Pacific
Paul H. Gross, University of the PacificFollow
Andreas H. Franz, University of the PacificFollow

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.

Recommended Citation

Chiu, T. M., Sigillo, K., Gross, P. H., & Franz, A. H. (2007). Synthesis of anomerically pure, furanose-free benzyl-2-amino-2-deoxy-mannuronic acid derivatives. Synthetic Communications, 37(14), 2355–2381. DOI: 10.1080/00397910701410871
https://scholarlycommons.pacific.edu/cop-facarticles/138