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)
Kim, Yong-Jae
This item is only available for download by members of the University of Illinois community. Students, faculty, and staff at the U of I may log in with your NetID and password to view the item. If you are trying to access an Illinois-restricted dissertation or thesis, you can request a copy through your library's Inter-Library Loan office or purchase a copy directly from ProQuest.
Permalink
https://hdl.handle.net/2142/84100
Description
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
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, Pharmaceutical
Language
eng
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.
Use this login method if you
don't
have an
@illinois.edu
email address.
(Oops, I do have one)
IDEALS migrated to a new platform on June 23, 2022. If you created
your account prior to this date, you will have to reset your password
using the forgot-password link below.
