Site-selective C-H Bond Diversification of Glycosides

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.

Name thesis:degree_name

Master

Department dc:contributor.department

Massachusetts Institute of Technology. Department of Chemistry

Grantor dc:publisher

Massachusetts Institute of Technology

Year dc:date.issued

2022

Author dc:creator

• Liu, Aaron

Advisor dc:contributor.advisor

• Wendlandt, Alison E.

Statement dc:rights

• In Copyright - Educational Use Permitted
• Copyright MIT

Licence dc:rights.uri

• http://rightsstatements.org/page/InC-EDU/1.0/

Handle dc:identifier.uri

https://hdl.handle.net/1721.1/144747

OAI identifier oai:identifier

oai:dspace.mit.edu:1721.1/144747