Synthesis of C-glycosyl-bis-1,2,3-triazole derivatives from 3,4,6-tri-O-acetyl-D-glucal

Mol Divers. 2015 Aug;19(3):423-34. doi: 10.1007/s11030-014-9564-0. Epub 2015 Jan 14.

Abstract

We have developed an efficient, CuI-catalyzed, microwave-assisted method for the synthesis of bis-1,2,3-triazole derivatives starting from a 3,4,6-tri-O-acetyl-D-glucal-derived mesylate. This mesylate was obtained from 3,4,6-tri-O-acetyl-D-glucal through C-glycosidation, deprotection of acetate groups to alcohols, and selective mesylation of the primary alcohol. This mesylate moiety was then converted to an azide through a microwave-assisted method with good yield. The azide, once synthesized, was then treated with different terminal alkynes in the presence of CuI to synthesize various bis-triazoles in high yields and short reaction times.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Chemistry Techniques, Synthetic
  • Click Chemistry
  • Copper / chemistry
  • Deoxyglucose / analogs & derivatives*
  • Deoxyglucose / chemistry
  • Glycosylation
  • Iodides / chemistry
  • Triazoles / chemical synthesis*
  • Triazoles / chemistry*

Substances

  • Iodides
  • Triazoles
  • 3,4,6-tri-O-acetylglucal
  • Copper
  • cuprous iodide
  • Deoxyglucose