Deoxy‐nitrosugars. 4th communication. Convenient synthesis of 1‐deoxy‐1‐nitroaldoses

Abstract

Abstract A new synthesis of 1‐deoxy‐1‐nitroaldoses by ozonolysis of N ‐glycosylnitrones according to the procedure of Bailey et al. is described. Based on the oxime 1 , the mannofuranosylnitrones 3–5 were obtained in yields of 86–88% and the 1‐deoxy‐1‐nitromannose 6 in yields of 70–76%. In the same manner the 1‐deoxy‐1‐nitroaldoses 9, 12, 18 , and 19 were prepared in yields of 61–90% from the oximes 7, 10, 14 and 15 , the procedure being compatible with the presence of free hydroxy groups.