{"id":{"repo_id":"mit","oai_identifier":"oai:dspace.mit.edu:1721.1/144747"},"canonical_url":"https://search.dev.ndltd.org/etd/mit/oai:dspace.mit.edu:1721.1/144747","repository":{"repo_id":"mit","name":"MIT","base_url":"https://dspace.mit.edu/oai/request"},"display":{"title":"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.","abstract_html":"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.","abstract_has_math":false,"creators":["Liu, Aaron"],"institution":"Massachusetts Institute of Technology","degree_name":"Master","degree_level":null,"degree_discipline":null,"degree_department":"Massachusetts Institute of Technology. Department of Chemistry","school":null,"contributors":[],"advisors":["Wendlandt, Alison E."],"committee_chairs":[],"committee_members":[],"year":2022,"date_issued":"2022-05","date_published":"2022-05","updated_at":"2026-07-22T22:21:48Z","subjects":[],"languages":[],"rights":["In Copyright - Educational Use Permitted","Copyright MIT"],"rights_urls":["http://rightsstatements.org/page/InC-EDU/1.0/"],"identifier_entries":[]},"links":{"outbound_url":"https://hdl.handle.net/1721.1/144747","outbound_label":"Handle","outbound_source":"dc:identifier.uri"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor.advisor","label":"Advisor","values":["Wendlandt, Alison E."]},{"key":"dc:contributor.department","label":"Department","values":["Massachusetts Institute of Technology. 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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."]},{"key":"dc:description.degree","label":"Dc Description Degree","values":["S.M."]},{"key":"dc:title","label":"Title","values":["Site-selective C-H Bond Diversification of Glycosides"]}]}],"canonical_facts":{"dc:contributor.advisor":["Wendlandt, Alison E."],"dc:contributor.department":["Massachusetts Institute of Technology. Department of Chemistry"],"dc:creator":["Liu, Aaron"],"dc:date.accessioned":["2022-08-29T16:08:57Z"],"dc:date.available":["2022-08-29T16:08:57Z"],"dc:date.issued":["2022-05"],"dc:description.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."],"dc:description.degree":["S.M."],"dc:identifier.uri":["https://hdl.handle.net/1721.1/144747"],"dc:publisher":["Massachusetts Institute of Technology"],"dc:rights":["In Copyright - Educational Use Permitted","Copyright MIT"],"dc:rights.uri":["http://rightsstatements.org/page/InC-EDU/1.0/"],"dc:title":["Site-selective C-H Bond Diversification of Glycosides"],"dc:type":["Thesis"],"thesis:degree_name":["Master","Master of Science in Chemistry"]},"updated_at":"2026-07-22T22:21:48Z"}