Gram-scale synthesis and efficient purification of 13C-labeled levoglucosan from 13C glucose

J Labelled Comp Radiopharm. 2013 Jan;56(1):27-9. doi: 10.1002/jlcr.2978. Epub 2012 Nov 14.

Abstract

(13)C-Labeled levoglucosan has been synthesized and purified in good yield, and on the gram scale in one step from commercially available (13)C glucose. This one-step protocol uses 2-chloro-1,3-dimethylimidazolinium chloride that serves to selectively activate the anomeric carbon toward substitution reactions. The labeled glucose is then smoothly converted to the anhydroglucose. Purification is efficiently achieved on large scale by chromatography on silica gel.

Keywords: 1,6-anhydroglucose; carbon-13 labeled; large scale; levoglucosan.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Carbon Isotopes / chemistry
  • Chemistry Techniques, Synthetic / methods
  • Glucose / analogs & derivatives*
  • Glucose / chemical synthesis
  • Glucose / isolation & purification

Substances

  • Carbon Isotopes
  • 1,6-anhydro-beta-glucopyranose
  • Glucose