Synthesis of anomerically pure, furanose-free benzyl-2-amino-2-deoxy-mannuronic acid derivatives
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.
Chiu, T. M.,
Gross, P. H.,
Franz, A. H.
Synthesis of anomerically pure, furanose-free benzyl-2-amino-2-deoxy-mannuronic acid derivatives.
Synthetic Communications, 37(14), 2355–2381.