One-Pot, Highly Stereoselective Synthesis of Dithioacetal-α,α-Diglycosides

Molecules. 2018 Apr 15;23(4):914. doi: 10.3390/molecules23040914.

Abstract

A one-step access to dithioacetal-α,α-diglycosides is reported. The synthetic strategy is based on the thioacetalization of aldehydes or ketones via highly stereoselective ring-opening of 1,6 anhydrosugars with bis(trimethylsilyl)sulfide.

Keywords: 1,6-anhydrosugars; dithioacetals; glycomimetics; ring-opening; thioglycosides.

MeSH terms

  • Chemistry, Organic / methods*
  • Glycosides / chemistry*
  • Ketones / chemistry
  • Molecular Conformation
  • Proton Magnetic Resonance Spectroscopy
  • Stereoisomerism

Substances

  • Glycosides
  • Ketones