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Date of Award

2002

Document Type

Dissertation - Pacific Access Restricted

Degree Name

Doctor of Philosophy (Ph.D.)

Department

Drug Discovery and Chemical Synthesis

First Advisor

Paul Gross

First Committee Member

Vyacheslav Samoshin

Second Committee Member

Donald Wedegaertner

Third Committee Member

Xiaoling Li

Abstract

Part I . Mechanistic intermediates were discovered in the Henry condensations of partially and non-protected pyranoses with a free anomeric hemiacetal function with nitromethane in various solvents for the syntheses of C-glycopyranosides in the presence of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU)/molecular sieves catalyst system. Part II . Syntheses of glycosyl cyanides were optimized with a new catalyst system. Mechanism of cyanation with trimethylsilyl cyanide (TMS-CN) in the presence of the mild and recyclable Lewis acid HgBr 2 in nitromethane were proposed for the syntheses of 1,2-trans per- O -acetylated C-glycopyranosyl cyanides. Part III . Tri-O-acetyl-β-L-fucopyranosyl cyanide and Pd-H 2 , in presence of BOC-anhydride, gave N-BOC-mono- and -di-(2,3,4-tri-O-acetyl-β-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-β-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as potentially useful synthon for preparation of more complex C-glycosidic conjugates.

Pages

129

ISBN

0493722181 , 9780493722184

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