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Date of Award
Dissertation - Pacific Access Restricted
Doctor of Philosophy (Ph.D.)
Drug Discovery and Chemical Synthesis
First Committee Member
Second Committee Member
Third Committee Member
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.
0493722181 , 9780493722184
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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