{"id":{"repo_id":"uiuc","oai_identifier":"oai:www.ideals.illinois.edu:2142/84115"},"canonical_url":"https://search.dev.ndltd.org/etd/uiuc/oai:www.ideals.illinois.edu:2142/84115","repository":{"repo_id":"uiuc","name":"University of Illinois - Urbana-Champaign","base_url":"https://www.ideals.illinois.edu/oai-pmh"},"display":{"title":"New Methodology for Alpha-Sialyl Glycoside Synthesis","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.","abstract_html":"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.","abstract_has_math":false,"creators":["Haberman, Jannine Michele"],"institution":"University of Illinois at Urbana-Champaign","degree_name":"Ph.D.","degree_level":"Dissertation","degree_discipline":"Chemistry","degree_department":null,"school":null,"contributors":["Gin, David Y."],"advisors":[],"committee_chairs":[],"committee_members":[],"year":2015,"date_issued":"2015-09-25T22:13:00Z","date_published":"2015-09-25T22:13:00Z","updated_at":"2026-07-22T22:26:22Z","subjects":["Chemistry, Organic"],"languages":["eng"],"rights":[],"rights_urls":[],"identifier_entries":[{"key":"dc:identifier","label":"Identifier","values":["(MiAaPQ)AAI3101852"],"render_values":[{"text":"(MiAaPQ)AAI3101852","href":null,"code":true}]}]},"links":{"outbound_url":"http://hdl.handle.net/2142/84115","outbound_label":"Handle","outbound_source":"dc:identifier"},"metadata_groups":[{"id":"people","label":"People","entries":[{"key":"dc:contributor","label":"Contributor","values":["Gin, David Y."]},{"key":"dc:creator","label":"Author","values":["Haberman, Jannine Michele"]}]},{"id":"academic_context","label":"Academic Context","entries":[{"key":"dc:date","label":"Dc Date","values":["2015-09-25T22:13:00Z","10000-01-01","2003"]},{"key":"dc:type","label":"Dc Type","values":["text"]},{"key":"thesis:degree_discipline","label":"Discipline","values":["Chemistry"]},{"key":"thesis:degree_level","label":"Degree Level","values":["Dissertation"]},{"key":"thesis:degree_name","label":"Degree Name","values":["Ph.D."]},{"key":"thesis:institution_name","label":"Thesis Institution Name","values":["University of Illinois at Urbana-Champaign"]}]},{"id":"subjects_keywords","label":"Subjects and Keywords","entries":[{"key":"dc:subject","label":"Dc Subject","values":["Chemistry, Organic"]}]},{"id":"language_rights","label":"Language and Rights","entries":[{"key":"dc:language","label":"Dc Language","values":["eng"]}]},{"id":"identifiers","label":"Identifiers","entries":[{"key":"dc:identifier","label":"Identifier","values":["http://hdl.handle.net/2142/84115","(MiAaPQ)AAI3101852"]}]},{"id":"additional","label":"Additional Metadata","entries":[{"key":"dc:description","label":"Description","values":["New methods for the synthesis of alpha-sialyl conjugates are presented. 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