The Journal of Organic Chemistry

Synthesis of acyclic sugar aldehydes by ozonolysis of oximes

DJ Weitz, MD Bednarski

Index: Weitz, David J.; Bednarski, Mark D. Journal of Organic Chemistry, 1989 , vol. 54, # 20 p. 4957 - 4959

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Citation Number: 14

Abstract

This note reports on an efficient method for the synthesis of acyclic sugar aldehydes based on the ozonolysis of methyloxime-protected aldoses. Readily accessible protected sugar oximes are converted into the corresponding aldehydo sugars in good yield and high purity on a multigram scale. This methodology eliminates problems associated with decomposition of these aldehydes by@-elimination and the formation of side products that contaminate ...