Boronate esters in oligosaccharide synthesis

Belogi, Gianluca (2000). Boronate esters in oligosaccharide synthesis. University of Birmingham. Ph.D.

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Abstract

This thesis describes novel applications of aryl boronic acid to the synthesis of oligosaccharides in solution and on solid phase. In solution phase synthesis, phenylboronic acid is a competent protecting group for both glycosyl donors and acceptors during glycosylation reactions. Polystyrylboronic acid, the polymeric counterpart of phenylboronic acid, is a useful solid support for the synthesis of oligosaccharides on solid phase. Disaccharides and trisaccharides can be synthesised in good yield and manipulation of protecting groups on solid phase can be performed. Ease of loading and ease of cleavage of the oligosaccharide moiety and its potential reusability are the most interesting features of this resin. These properties also allow the development of a strategy that overcomes the problem of controlling the stereochemical outcome of every glycosylation during the synthesis of a complex oligosaccharide conducted on solid support. An anomeric mixture of oligosaccharides is easily cleaved from the support and, after separation of the anomers and reloading of only one anomer on the resin, the synthetic sequence is continued. A trisaccharide was synthesised by employing this methodology.

The second aim of this thesis is to investigate some aspects of the structure of boronate esters of carbohydrates.

Type of Work:

Thesis (Doctorates > Ph.D.)

Award Type:

Doctorates > Ph.D.

Supervisor(s):