With the increasing realization of their involvement in numerous biological processes, synthetic oligosaccharides present promising potential in drug and vaccine discovery. Selective functionalization of hydroxy groups in polyols represent a long-standing goal in chemistry since the chemical synthesis of O-glycosides often requires extensive protecting group manipulation. Organoboron catalysis is a recent strategy for regioselective activation of the equatorial hydroxy group of cis-vicinal diols. Following the initial findings that diarylborinic acid catalyzes the regioselective acylation of carbohydrate derivatives, kinetic studies were conducted to obtain better insight on the mechanism. Thereafter, the ability of diarylborinic acid to catalyze the regioselective alkylation of carbohydrates was demonstrated. Finally, investigations in the capability of diarylborinic acid to influence regiochemical outcome of glycosylation reactions were explored. Similarly, kinetic experiments were devised to shed light on the mechanism of the reaction.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/30538 |
| Date | 05 December 2011 |
| Creators | Chan, Lina |
| Contributors | Taylor, Mark S. |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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