Conformationally superarmed S-ethyl glycosyl donors as effective building blocks for chemoselective oligosaccharide synthesis in one pot

Org Biomol Chem. 2017 Jan 18;15(3):559-563. doi: 10.1039/c6ob02498j.

Abstract

A new series of superarmed glycosyl donors has been investigated. It was demonstrated that the S-ethyl leaving group allows for high reactivity, which is much higher than that of equally equipped S-phenyl glycosyl donors that were previously investigated by our groups. The superarmed S-ethyl glycosyl donors equipped with a 2-O-benzoyl group gave complete β-stereoselectivity. Utility of the new glycosyl donors has been demonstrated in a one-pot one-addition oligosaccharide synthesis with all of the reaction components present from the beginning.

MeSH terms

  • Carbohydrate Conformation
  • Glycosides / chemistry*
  • Glycosylation
  • Oligosaccharides / chemical synthesis*
  • Oligosaccharides / chemistry
  • Stereoisomerism

Substances

  • Glycosides
  • Oligosaccharides