Site-selective C-H Bond Diversification of Glycosides

Abstract

Synthetic carbohydrates have recently emerged as an important motif in the development of modern therapeutics. Despite the biological significance of carbohydrate mimetics, synthetic challenges continue to limit the widespread implementation of these compounds. The thesis presented herein includes three specific sections with the ultimate goal of developing a general, selective and efficient catalytic system for monosaccharide functionalization: 1) site-selective halogenation & derivatization of sugars, 2) expedient synthesis of L-glucose and 3) diastereoselective C-H alkylation of sugars. These radical-based transformations harness polarity compatibility between the hydrogen atom abstractor and the substrate to afford site-selective functionalization of sugars that have broad potential biomedical value.