New Stereoselective Thioglycosylation Method

  • Author: Chemistry – A European Journal
  • Published Date: 17 November 2019
  • Source / Publisher: Chemistry – A European Journal/Wiley-VCH
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
thumbnail image: New Stereoselective Thioglycosylation Method

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Thioglycosides are useful mimetics for natural carbohydrates. This is due to their stability to enzymatic hydrolysis and their close similarity to the natural O-glycosides. While many strategies exist for the synthesis of 1,2-trans-thio-linked glycomimetics, a general synthetic method for the analogous 1,2-cis-thio-linked glycosides had not yet been developed.

Anikó Borbás, University of Debrecen, Hungary, and colleagues have found that a radical-mediated thiol-ene coupling reaction of 1,2-unsaturated sugars, or glycals, can be used as a new stereoselective thioglycosylation method. Three types of acetylated glycals were reacted with a broad range of thiols under UV irradiation at temperatures between –120 °C and room temperature.

The team found that the reactions proceed with 1,2-cis-stereoselectivity and generally with high yield. Cooler temperatures were beneficial to the reaction. According to the researchers, these low-temperature thiol-ene coupling reactions provide a complementary strategy to existing methods for the synthesis of thioglycosides.



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Magazine of Chemistry Europe (16 European Chemical Societies) published by Wiley-VCH