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Title:New Methodology for Alpha-Sialyl Glycoside Synthesis
Author(s):Haberman, Jannine Michele
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:New methods for the synthesis of alpha-sialyl conjugates are presented. A novel N,N-dimethylglycolamide ester auxiliary has been incorporated at the C1-position of sialyl donors, allowing for C1-neighboring group participation to generate sialyl conjugates with good to excellent alpha-selectivity under a variety of sialylation protocols. This C1-auxiliary has also been used in the development of the dehydrative sialylation, employing the reagent combination of (p-nitrophenyl)(phenyl) sulfoxide and trifluoromethane-sulfonic anhydride. The dehydrative sialylation method establishes C2-hemiketals as a new class of sialyl donor for complex carbohydrate synthesis. Efforts to apply these new strategies to the synthesis of the trisaccharide portion of ganglioside GM3 are also discussed.
Issue Date:2003
Type:Text
Language:English
Description:217 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2003.
URI:http://hdl.handle.net/2142/84115
Other Identifier(s):(MiAaPQ)AAI3101852
Date Available in IDEALS:2015-09-25
Date Deposited:2003


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