Login / Signup

Facile triflic acid-catalyzed α-1,2-cis-thio glycosylations: scope and application to the synthesis of S-linked oligosaccharides, glycolipids, sublancin glycopeptides, and TN/TF antigens.

Sanyong ZhuGanesh SamalaEric T SlettenJennifer L StockdillHien M Nguyen
Published in: Chemical science (2019)
Studies of S-linked glycoconjugates have attracted growing interest because of their enhanced chemical stability and enzymatic resistance over O-glycoside counterparts. We here report a facile approach to access α-1,2-cis-S-linked glycosides using triflic acid as a catalyst to promote the glycosylation of a series of thiols with d-glucosamine, galactosamine, glucose, and galactose electrophiles. This method is broadly applicable for the stereoselective synthesis of S-linked glycopeptides, oligosaccharides and glycolipids in high yield and excellent α-selectivity. Many of the synthetic limitations associated with the preparation of these S-linked products are overcome by this catalytic method.
Keyphrases
  • highly efficient
  • room temperature
  • metal organic framework
  • dendritic cells
  • immune response
  • ionic liquid
  • adipose tissue
  • blood pressure
  • mass spectrometry
  • high resolution
  • gold nanoparticles