ortho-(Methyltosylaminoethynyl)benzyl glycosides as new glycosyl donors for latent-active glycosylation

Chem Commun (Camb). 2015 Sep 21;51(73):13957-60. doi: 10.1039/c5cc05651a.

Abstract

A new glycosylation protocol employing ortho-(methyltosylaminoethynyl)benzyl glycosides as glycosyl donors and TMSOTf as the catalyst is disclosed. These donors can be readily prepared from the corresponding 'latent' ortho-iodobenzyl glycosides via a Sonogashira coupling, thus providing a new approach for the 'latent-active' synthesis of glycans.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Glycosides / chemistry*
  • Glycosylation
  • Mesylates / chemistry
  • Trimethylsilyl Compounds / chemistry

Substances

  • Glycosides
  • Mesylates
  • Trimethylsilyl Compounds
  • trimethylsilyl trifluoromethanesulfonate