New Methods for the Site-selective O-H and C-H Functionalization of Sugars
Abstract
Carbohydrates are among the most abundant biomolecules in nature and serve as the metabolic precursors to nearly all other biomolecules. The immense structural diversity found among carbohydrates has resulted in an equally diverse profile of biological functions, including roles in energy storage, structural support, and cell-cell communication. Recognizing the myriad of vital roles carbohydrates serve in animals, development of carbohydrate-based drugs has been pursued intensely and has resulted in the prolific use of drugs like empagliflozin, enoxaparin and molnupiravir. The function of most natural carbohydrates is unknown and glycobiological research on them is limited by their availability. To facilitate this research, new synthetic methods able to generate the sophisticated functionalization patterns found in these molecules must be developed. Direct methods for the site-selective installation of functional groups onto carbohydrates are desired as they avoid the process inefficiencies caused by use of protecting groups. In this thesis, new catalytic methods for the site-selective O-H functionalization of carbohydrates will be covered. Chapter 1 will cover the borinic-acid catalyzed sulfation of carbohydrates and Chapter 2 will cover the boronic-acid catalyzed sulfamoylation of carbohydrates. Photoredox catalysis has resulted in the revitalization of radical chemistry by enabling access to open-shell intermediates under mild conditions. In conjunction with hydrogen atom…
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