通过光延反应立体选择性合成含硒糖缀合物

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

Department of Chemical Sciences, University of Napoli Federico II, Via Cintia 4, I-80126 Napoli, Italy.

Department of Sciences, University of Basilicata, Via dell'Ateneo Lucano 10, I-85100 Potenza, Italy.

Molecules. 2021 Apr 27;26(9):2541. doi: 10.3390/molecules26092541.

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.

一种用于合成新型糖缀合物的简单高效方法已被开发出来。该方法可作为一个化合物微型文库的模型，这些化合物具有与具有著名抗氧化特性的多酚部分相连的脱氧硒糖核心。在光延关键反应中检测到的意外立体控制导致了最具吸引力的具有天然d构型的产物。因此，我们能够通过更短且便捷的反应序列从市售的d-核糖获得目标分子。