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Article
Synthesis of anomerically pure, furanose-free benzyl-2-amino-2-deoxy-mannuronic acid derivatives
Synthetic Communications
  • Tony M. K. Chiu, University of the Pacific
  • Katina Sigillo, University of the Pacific
  • Paul H. Gross, University of the Pacific
  • Andreas H. Franz, University of the Pacific
Document Type
Article
Department
Chemistry
DOI
10.1080/00397910701410871
Publication Date
1-1-2007
Disciplines
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.
Citation Information
Tony M. K. Chiu, Katina Sigillo, Paul H. Gross and Andreas H. Franz. "Synthesis of anomerically pure, furanose-free benzyl-2-amino-2-deoxy-mannuronic acid derivatives" Synthetic Communications Vol. 37 Iss. 14 (2007) p. 2355 - 2381 ISSN: 0039-7911
Available at: http://works.bepress.com/andreas-franz/74/