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Title:I. Sulfonium-Mediated Oxidative Glycosylation of Glycal Donors for the Synthesis of C(2)-Hydroxy-Beta-Glycosides. II. Hypervalent Iodine (iii)-Mediated Oxidative Glycosylation of Glycal Donors for the Synthesis of C(2)-Acyloxy-Beta-Glycosides. III. Efforts Toward the Synthesis of Immunologic Adjuvant Qs-21a(api)
Author(s):Kim, Yong-Jae
Doctoral Committee Chair(s):Gin, David Y.
Department / Program:Chemistry
Degree Granting Institution:University of Illinois at Urbana-Champaign
Subject(s):Chemistry, Pharmaceutical
Abstract:Development of two novel glycosylation procedures, and the synthesis of immunologic adjuvant QS-21Aapi is reported. In the first glycosylation procedure, glycals were employed as glycosyl donors and activated with a reagent combination of diphenyl sulfoxide and triflic anhydride. This sulfonium-mediated oxidative glycosylation procedure can be used for 1,2-trans-C2-hydroxy-beta-glycoside synthesis with the application to assemble C2-branched oligosaccharides. In the second glycosylation procedure, glycals were activated with bisacyliodobenzene and boron trifluoride diethyl etherate for the synthesis of 1,2-trans -C2-acyloxy-beta-glycoside with the application to assemble non-C2-branched oligosaccharides. In the third section of this thesis, an acylated triterpene glycoside QS-21Aapi was targeted for synthesis using the two oxidative glycosylation procedures as well as a sulfonium-mediated dehydrative glycosylation procedure. Synthesis and extraction of the four components of the saponin, which includes a trisaccharide, a tetrasaccharide, a triterpene and an acyl side chain were accomplished leading to the assembly of these four components to provide the fully protected QS-21Aapi.
Issue Date:2003
Description:263 p.
Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2003.
Other Identifier(s):(MiAaPQ)AAI3086101
Date Available in IDEALS:2015-09-25
Date Deposited:2003

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