This thesis is divided into four chapters. The first contains an introduction to oligosaccharides, including an overview of their role in nature and a summary of the difficulties and complexities in saccharide synthesis in the context of protection strategies. Selective glycosylation reactions, by control of donor reactivity, and the development of the armed/disarmed concept for saccharide coupling are discussed. The second chapter concerns research into the scope of selective glycosylations using competition reactions to evaluate the effects of protecting groups on the reactivity of glycosyl donors. A variety of protecting groups are studied with both rhamnose and mannose monosaccharides. The influence of the sugar type and of different anomeric leaving groups is also discussed. The third chapter deals with the application of data from chapter 2 to the design of oligosaccharide syntheses. A trisaccharide synthesis is planned whereby the protecting group strategy is developed to tune the reactivity of the monosaccharide building blocks. This enabled a "one-pot" procedure to be implemented, demonstrating the suitability of this methodology to the efficient synthesis of oligosaccharides.
| Identifer | oai:union.ndltd.org:bl.uk/oai:ethos.bl.uk:598613 |
| Date | January 1997 |
| Creators | Douglas, N. L. |
| Publisher | University of Cambridge |
| Source Sets | Ethos UK |
| Detected Language | English |
| Type | Electronic Thesis or Dissertation |
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