Synthesis of anomerically pure, furanose-free benzyl-2-amino-2-deoxy-mannuronic acid derivativesSynthetic Communications
AbstractThe 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 InformationTony 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/