Use this URL to cite or link to this record in EThOS:
Title: Tuning glycoside reactivity : a new tool for efficient oligosaccharide synthesis
Author: Douglas, N. L.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 1997
Availability of Full Text:
Full text unavailable from EThOS.
Please contact the current institution’s library for further details.
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.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available