Synthesis of Salmonella enteritidis Antigenic Tetrasaccharide Repeating Unit by Employing Cationic Gold(I)-Catalyzed Glycosylation Involving Glycosyl N-1,1-Dimethylpropargyl Carbamate Donors

J Org Chem. 2024 Sep 6;89(17):12547-12558. doi: 10.1021/acs.joc.4c01484. Epub 2024 Aug 13.

Abstract

Synthesis of an antigenic tetrasaccharide repeating unit of the O-polysaccharide of Salmonella enteritidis lipopolysaccharide has been accomplished. Those four monosaccharides were assembled stereoselectively by employing our recently developed cationic gold(I)-catalyzed glycosylation methodology involving various glycosyl N-1,1-dimethylpropargyl carbamate donors. The newly formed α-anomeric stereochemical configuration was controlled by the axial C2-OBz of the glycosyl donors via anchimeric assistance.

Publication types

  • Research Support, N.I.H., Extramural

MeSH terms

  • Carbamates* / chemistry
  • Catalysis
  • Cations / chemistry
  • Glycosylation
  • Gold* / chemistry
  • O Antigens / chemistry
  • Oligosaccharides* / chemical synthesis
  • Oligosaccharides* / chemistry
  • Salmonella enteritidis* / chemistry
  • Stereoisomerism

Substances

  • Gold
  • Carbamates
  • Oligosaccharides
  • Cations
  • O Antigens