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A Short and Economical Synthesis of Orthogonally Protected C-Linked 2-Deoxy-2-acetamido-alpha-d-galactopyranose Derivatives.

Bouvet VR, Ben RN

Department of Chemistry, University of Ottawa, Ottawa, Ontario KIN 6N5, Canada robert.ben@science.uottawa.ca.

A short and high-yielding synthesis has been devised to prepare C-linked 2-deoxy-2-acetamido-alpha-d-galactopyranose derivative 3. One of the main advantages of this approach is that it employs commercially available and inexpensive d-glucosamine as the starting material. The key steps include a highly stereoselective C-allylation followed by epimerization of the C-4 hydroxyl group. Building block 3 and orthogonally protected C-linked 2-deoxy-2-acetamido-alpha-d-galactopyranose derivative 2 were obtained in 44% overall yield (six steps) and 29% overall yield (eight steps), respectively. This represents a significant improvement over previously reported syntheses.

Published 21 April 2006 in J Org Chem, 71(9): 3619-22.
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