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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 |
Discipline: | Chemistry |
Degree Granting Institution: | University of Illinois at Urbana-Champaign |
Degree: | Ph.D. |
Genre: | Dissertation |
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 |
Type: | Text |
Language: | English |
Description: | 263 p. Thesis (Ph.D.)--University of Illinois at Urbana-Champaign, 2003. |
URI: | http://hdl.handle.net/2142/84100 |
Other Identifier(s): | (MiAaPQ)AAI3086101 |
Date Available in IDEALS: | 2015-09-25 |
Date Deposited: | 2003 |
This item appears in the following Collection(s)
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Dissertations and Theses - Chemistry
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Graduate Dissertations and Theses at Illinois
Graduate Theses and Dissertations at Illinois