2-Deoxy sugars are an important class of carbohydrates which exist in a wide range of bioactive natural products and have been found to play vital role in biological activity of those natural molecules. Due to limited amounts of these molecules can be isolated from natural sources, it is critical to develop efficient approach for stereoselective synthesis of 2-deoxy sugars in order to extensively study their structure and activity relationship for discovery of effective therapeutic agents. Despite a number of synthetic studies have been previously reported, stereoselective synthesis of 2-deoxy-glycosides still remains very challenging because of the lack of directing group at C-2 position. We have outlined a novel method for the stereoselective synthesis of 2-deoxy-glycosides which involves reaction of 2-deoxy glycosyl lithium species with sugar-derived peroxides. Preliminary results have demonstrated that reactions of both a- and �- glycosyl lithium with sugar-derived peroxide at low temperature selectively afford 2-deoxy- a- and �- oligosaccharides, respectively.

Umpolung reactivity in stereoselective synthesis of 2-deoxy glycosides

244th National Meeting (2012)

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