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

Vincent R. Bouvet and Robert N. Ben*
Department of Chemistry, University of Ottawa, Ottawa, Ontario KIN 6N5, Canada robert.ben@science.uottawa.ca
J. Org. Chem., 2006, 71 (9), pp 3619–3622
DOI: 10.1021/jo051938j
Publication Date (Web): April 6, 2006
Copyright © 2006 American Chemical Society
*

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

Abstract

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A short and high-yielding synthesis has been devised to prepare C-linked 2-deoxy-2-acetamido-α-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-α-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.

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History

  • Published In Issue April 28, 2006
  • Received September 15, 2005

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