Molecules (Apr 2021)

Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction

  • Luigia Serpico,
  • Mauro De Nisco,
  • Flavio Cermola,
  • Michele Manfra,
  • Silvana Pedatella

DOI
https://doi.org/10.3390/molecules26092541
Journal volume & issue
Vol. 26, no. 9
p. 2541

Abstract

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A simple and efficient route for the synthesis of new glycoconjugates has been developed. The approach acts as a model for a mini-library of compounds with a deoxy-selenosugar core joined to a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontrol detected in the Mitsunobu key reaction led to the most attractive product showing a natural d-configuration. Thus, we were able to obtain the target molecules from the commercially available d-ribose via a shorter and convenient sequence of reactions.

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