Synthesis of double C-glycoside analogue of sTn

J Org Chem. 2005 Sep 30;70(20):8197-200. doi: 10.1021/jo050691n.

Abstract

A sTn double C-glycoside, sTn analogue 2, was synthesized using samarium chemistry developed in our laboratory. Complications in the oxidation reaction affording aldehyde acceptor were overcome by double protection of amide and the use of a room-temperature ionic liquid as solvent. Studies are underway to conjugate the sTn double C-glycoside hapten 2 to KLH carrier protein for biological evaluation as a vaccine.

MeSH terms

  • Carbohydrate Conformation
  • Disaccharides / chemical synthesis*
  • Disaccharides / chemistry
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry*
  • Indicators and Reagents
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Molecular Structure
  • Neuraminic Acids / chemistry
  • Sialic Acids*
  • Tin*

Substances

  • Disaccharides
  • Glycosides
  • Indicators and Reagents
  • Neuraminic Acids
  • Sialic Acids
  • Tin