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Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction
Authors:Luigia Serpico  Mauro De Nisco  Flavio Cermola  Michele Manfra  Silvana Pedatella
Affiliation:1.Department of Chemical Sciences, University of Napoli Federico II, Via Cintia 4, I-80126 Napoli, Italy; (L.S.); (F.C.); (S.P.);2.Department of Sciences, University of Basilicata, Via dell’Ateneo Lucano 10, I-85100 Potenza, Italy;
Abstract: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.
Keywords:organoselenium compounds   selenosugar   mitsunobu reaction   antioxidants
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