Site-selective C-H Bond Diversification of Glycosides
Name
Liu-aaronliu-sm-chemistry-2022-thesis.pdf
Description
Thesis PDF
Size
1.06 MB
Format
Adobe PDF
Checksum (MD5)
e7281d51240023bf44b4da1db8140ab3
Author(s)
Liu, Aaron
Advisor(s)
Wendlandt, Alison E.
Date Issued
May 2022
Publisher
Massachusetts Institute of Technology
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.
MIT Department
Massachusetts Institute of Technology. Department of Chemistry
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