Investigation of benzoyloximes as benzoylating reagents: benzoyl-Oxyma as a selective benzoylating reagent

Org Biomol Chem. 2016 Jan 7;14(1):97-104. doi: 10.1039/c5ob02092a. Epub 2015 Nov 4.

Abstract

Hydroxybenzotriazole (HOBt) and HOBt-derived reagents have been classified as Class I explosives, with restrictions on their transportation and storage. We explored a range of benzoylated oxime-based reagents as alternatives to benzoyloxybenzotriazole (BBTZ) for the selective benzoylation of carbohydrate polyols. Benzoylated oximes derived from 2-hydroximino-malononitrile, ethyl 2-hydroximino-2-cyanoacetate (Oxyma), and tert-butyl 2-hydroximino-2-cyanoacetate were most effective for benzoylation of a simple primary alcohol, with yields approaching that obtained for BBTZ. When applied to carbohydrate diols, the most effective reagent was identified as benzoyl-Oxyma. Benzoyl-Oxyma is a highly crystalline, readily prepared alternative to BBTZ, useful in the selective benzoylation of carbohydrate polyols.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Indicators and Reagents
  • Models, Molecular
  • Molecular Structure
  • Oximes / chemistry*
  • Pregnadienes / chemistry*
  • Triazoles / chemistry

Substances

  • 1-(benzoyloxy)benzotriazole
  • Indicators and Reagents
  • Oximes
  • Pregnadienes
  • Triazoles
  • oxyma