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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 37, 2007 - Issue 14
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Original Articles

Synthesis of Anomerically Pure, Furanose‐Free α‐Benzyl‐2‐amino‐2‐deoxy‐d‐altro‐ and d‐manno‐pyranosides and Some of Their Derivatives

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Pages 2355-2381 | Received 08 Dec 2006, Published online: 11 Jul 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.

Acknowledgments

We express gratitude for the financial support of K. S. (undergraduate research participant) through a Dreyfus Senior Scientist Mentor Grant to P. H. G. and through a College of the Pacific Dean's Research Award.

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