New Methodology for Alpha-Sialyl Glycoside Synthesis

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.

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 dc:creator

• Haberman, Jannine Michele

Contributors dc:contributor

• Gin, David Y.

• Chemistry, Organic

Language dc:language

eng

Identifier

(MiAaPQ)AAI3101852

OAI identifier oai:identifier

oai:www.ideals.illinois.edu:2142/84115