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Abstract
A method for the preparation of C-methyl branched nitro sugars from the corresponding amino sugars by oxidation with mixed oxidants is described. Ozonolysis of the amino sugars in the presence of OXONE (potassium monopersulfate) and acetone (Bashir-Hashemi's procedure) gave nitro sugars in good yields. Oxidation of an O-benzylhydroxylamino sugar by this method resulted in deprotection and oxidation in a single step, giving the nitro sugar directly. The mixed oxidant method is experimentally simpler and more convenient to use than DMDO, which had been previously reported for the oxidation of amino sugars.
ACKNOWLEDGMENTS
The authors thank the Petroleum Research Fund, administered by the American Chemical Society, and Villanova University for financial support of this research.