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Title:Development and Investigation of a Dehydrative Glycosylation With Activated Diphenyl Sulfonium Reagents
Author(s):Garcia, Brian Allen
Doctoral Committee Chair(s):Gin, David Y.
Department / Program:Chemistry
Discipline:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Degree:Ph.D.
Genre:Dissertation
Subject(s):Chemistry, Organic
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.
Issue Date:2001
Type:Text
Language:English
Description:104 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2001.
URI:http://hdl.handle.net/2142/84506
Other Identifier(s):(MiAaPQ)AAI9996634
Date Available in IDEALS:2015-09-25
Date Deposited:2001


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