Development and Investigation of a Dehydrative Glycosylation With Activated Diphenyl Sulfonium Reagents
Garcia, Brian Allen
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https://hdl.handle.net/2142/84506
Description
Title
Development and Investigation of a Dehydrative Glycosylation With Activated Diphenyl Sulfonium Reagents
Author(s)
Garcia, Brian Allen
Issue Date
2001
Doctoral Committee Chair(s)
Gin, David Y.
Department of Study
Chemistry
Discipline
Chemistry
Degree Granting Institution
University of Illinois at Urbana-Champaign
Degree Name
Ph.D.
Degree Level
Dissertation
Keyword(s)
Chemistry, Organic
Language
eng
Abstract
Mechanistic 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.
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