S-glycosides in medicinal chemistry: Novel synthesis of cyanoethylene thioglycosides and their pyrazole derivatives

Nucleosides Nucleotides Nucleic Acids. 2017 Mar 4;36(3):198-212. doi: 10.1080/15257770.2016.1257807. Epub 2017 Jan 3.

Abstract

A one-pot reaction of a sodium 2-cyanoethylene-1-thiolate salt with 2,3,4,6-tetra-O-acetyl-α-D-gluco- and galactopyranosyl bromides affords a new class of cyanoethylene thioglycosides. The conversion to the corresponding 5-aminopyrazoles confirms the E-configuration of these cyanoethylene thioglycosides.

Keywords: Cyanoethylene; cyanoethylene thioglycosides; pyrazoles; sodium 2-cyanoethylene-1-thiolate salts; thioglycosides.

MeSH terms

  • Chemistry Techniques, Synthetic
  • Chemistry, Pharmaceutical / methods
  • Ethylenes / chemistry
  • Glycosides / chemical synthesis*
  • Glycosides / chemistry
  • Magnetic Resonance Spectroscopy
  • Pyrazoles / chemistry
  • Thioglycosides / chemical synthesis

Substances

  • Ethylenes
  • Glycosides
  • Pyrazoles
  • Thioglycosides