Umpolung Reactivity in Stereoselective Synthesis of 2-Deoxy Glycosides and Thioglycosides

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In this project funded by the Chemical Synthesis Program of the Chemistry Division, Professor Jianglong Zhu of the Department of Chemistry at University of Toledo will develop umpolung reactivity-based glycosylations for stereoselective syntheses of biologically important 2-deoxy glycosides and thioglycosides. Despite recent accomplishments in the development of glycosylation methodology, stereoselective synthesis of 2-deoxy sugars remains challenging because of the lack of a directing group at the C-2 position. This project focuses on investigating reactions of stereochemically defined 2-deoxy glycosyl anions with sugar-derived peroxo and disulfide acceptors for stereoselective preparation of 2-deoxy glycosides and thioglycosides. In addition, experimental efforts will be taken to understand the mechanism of these umpolung reactivity-based glycosylations. Successful accomplishment of this project will have a significant impact on synthetic organic community, because it will provide a strategy that complements current methods in the stereoselective synthesis of structurally challenging and biologically valuable 2-deoxy glycosides and thioglycosides. This project could lead to the synthesis of a variety of sugar based therapeutic agents. In addition, it will provide excellent training for undergraduate and graduate students, K-12 science teachers, and high school students, including those from groups currently underrepresented in the chemical sciences.