The realization that oligosaccharides play a central role in many biological processes has led to increasing interest in the preparation of synthetic targets for use in medical or biochemical research and drug discovery. The preparation of oligosaccharides from simple carbohydrate derivatives requires efficient methods for the construction of O-glycosidic bonds. Much effort has been made towards the development of selective methods for the preparation of oligosaccharide targets. The most common method to overcome the challenge of regioselectivity is the use of protecting group manipulations to suppress glycosylation at undesired positions. This is highly inefficient in terms of atom and step economy. Organoboron catalysis is a recent strategy that imparts regioselective activation of the equatorial hydroxy group of cis-vicinal diols towards functionalization. Following the initial findings that diarylborinic acid catalyzes the regioselective acylation of carbohydrate derivatives, an analogous method for regioselective glycosylation under Koenigs-Knorr conditions has been developed.
| Identifer | oai:union.ndltd.org:TORONTO/oai:tspace.library.utoronto.ca:1807/30613 |
| Date | 07 December 2011 |
| Creators | Gouliaras, Christina |
| Contributors | Taylor, Mark S. |
| Source Sets | University of Toronto |
| Language | en_ca |
| Detected Language | English |
| Type | Thesis |
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