Nucleophilic Opening of N-Carboalkoxy-2, 3-anhydro-1-deoxymannojirimycin. A Useful Method for the Syntheses of 2-, 3-and 2, 3-Disubstituted 1-Deoxynojirimycin …

…, FJ Koszyk, MA Stealey, RM Weier, J Julien…

Index: Khanna, Ish K.; Koszyk, Francis J.; Stealey, Michael A.; Weier, Richard M.; Julien, Janet; et al. Journal of Carbohydrate Chemistry, 1995 , vol. 14, # 6 p. 843 - 878

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Citation Number: 12

Abstract

Abstract A useful methodology for the synthesis of a number of 2-, 3-and 2, 3-disubstituted deoxynojirimycin analogs is reported. It has been found that the epoxides in stereoselectively synthesized N-carboalkoxy-2, 3-anhydro-1-deoxymannojirimycins (4 and 5) react with N-, S-and F-nucleophiles to give a mixture of gluco and altro products. The 3- azido altro compound (12b) yields the desired gluco derivative (40) by oxidation, in situ ...