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University of Illinois at Urbana-Champaign
Development and Investigation of a Dehydrative Glycosylation With Activated Diphenyl Sulfonium Reagents
Abstract
dc:descriptionMechanistic studies suggest that the glycosyl donor is initially activated via nucleophilic attack of the hemiacetal hydroxyl upon the sulfonium center of diphenylsulfide bis(trifluoromethanesulfonate), leading to formation of a glycosyl oxosulfonium. Low temperature NMR studies have revealed that a glycosyl pyridiniurn is subsequently formed in the latter stages of the glycosylation. Additional data suggests, however, that the reactive intermediate is likely a glycosyl oxocarbenium.
Degree
thesis:*- Name thesis:degree_name
- Ph.D.
- Level thesis:degree_level
- Dissertation
- Discipline thesis:degree_discipline
- Chemistry
- Grantor
- University of Illinois at Urbana-Champaign
- Year dc:date
- 2015
Author and committee
dc:creator, dc:contributor.*- Author dc:creator
-
- Garcia, Brian Allen
- Contributors dc:contributor
-
- Gin, David Y.
Subjects
dc:subject × 1Rights
- Language dc:language
- eng
Identifiers
dc:identifier.*- Identifier
- (MiAaPQ)AAI9996634
- OAI identifier oai:identifier
- oai:www.ideals.illinois.edu:2142/84506