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

University Of Toledo, Toledo OH

Investigators

Abstract

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.