Synthesis of 2-C-substituted and 1,2-C,C-disubstituted glycal derivatives and their thiol-ene addition reactions

Abstract

During the investigation of 1-C-substituted glycals (5), our research group developed a simple method for the preparation of 2-iodo derivatives (6) and for the synthesis of 1,2-C,C-disubstituted glycal derivatives (7) using a Suzuki–Miyaura type cross-coupling reaction. As a continuation of this work, we intend to investigate the transformation of derivatives (7) under the conditions of a photoinitiated thiol-ene addition reaction to afford compounds (14) and (15), and study the regio- and stereoselectivity of the reaction. In the case of the prepared compounds, there is also the possibility of performing biological studies, such as lectin inhibition and evaluation as potential galectin inhibitors, within the framework of international cooperation.