Visible-Light-Promoted Desulfurization to Synthesize Deoxyglycosides

J Org Chem. 2023 Jul 7;88(13):8024-8033. doi: 10.1021/acs.joc.3c00046. Epub 2023 May 25.

Abstract

In this study, we have successfully applied a visible-light-promoted desulfurization method to the synthesis of deoxysugars, especially 1-deoxyglycose, 2,4-deoxyglycosides, and 2-deoxyglycosides with exclusive α-configuration. Compared to the reported desulfurization under UV light (500 W mercury lamp), this desulfurization under visible light (20 W blue LED) is easy to operate since it does not require a dedicated photochemical reactor, occurs under very mild conditions, and is able to avoid many of the side reactions that often occur during the UV-induced desulfurization.

MeSH terms

  • Glycosides / chemistry
  • Light
  • Oxidation-Reduction
  • Sulfides* / chemistry

Substances

  • Sulfides
  • Glycosides