New Methodology for Alpha-Sialyl Glycoside Synthesis
Haberman, Jannine Michele
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https://hdl.handle.net/2142/84115
Description
Title
New Methodology for Alpha-Sialyl Glycoside Synthesis
Author(s)
Haberman, Jannine Michele
Issue Date
2003
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
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.
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