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Date of Award

2000

Document Type

Dissertation - Pacific Access Restricted

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Chemistry

First Advisor

Paul Gross

First Committee Member

James Blankenship

Second Committee Member

Charles Matuzak

Third Committee Member

Vyacheslav Samoshin

Fourth Committee Member

Donald Wedegaertner

Abstract

In view of the significance of oligosaccharides in biological processes and the distinct disadvantage of easy metabolic degradation by glycosidases, a synthetic effort to prepare oligosaccharide mimics with enhanced metabolic stability was undertaken. This thesis introduces a new methodology for a high-yielding synthesis of mono- or oligosaccharidic glycals under non-solvolytic conditions. Lewis acid promoted glycal dimerization followed by introduction of a glycosyl cyanide functionality converted the compounds into possible anchors for pharmacophores. The experiments are discussed with respect to general applicability of the synthetic methods, stereoselectivity, and the biological properties of the compounds.

Pages

299

ISBN

9780599838109 , 0599838108

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