Stereoselective Synthesis of Selenium-Containing Glycoconjugates via the Mitsunobu Reaction

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 joinedto a polyphenolic moiety with well-known antioxidant properties. An unexpected stereocontroldetected in the Mitsunobu key reaction led to the most attractive product showing a natural Dconfiguration. Thus, we were able to obtain the target molecules from the commercially availableD-ribose via a shorter and convenient sequence of reactions