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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
Recommended Citation
Phiasivongsa, Pasit. (2002). Synthesis of saccharomimetic fucopyranosyl -substituted urethanes and ureas from glycopyranosyl nitromethanes and cyanides. University of the Pacific, Dissertation - Pacific Access Restricted. https://scholarlycommons.pacific.edu/uop_etds/2699
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