Uronic acids in oligosaccharide synthesis

Author(s):
Bos, L.J. van den
Published
2007
Publication type
Doctoral Thesis

Abstract

This Thesis reports on research aimed at the assembly of acidic and zwitterionic polysaccharides of bacterial origin, using suitably protected 1-thioglycoside residues. Thioglycosides are attractive monosaccharide building blocks because of their high stability towards the diverse reaction conditions used in functional group manipulations. Recently, the use of 1-thioglycosides has been stimulated by the advent of the 1-benzenesulfinylpiperidine (BSP)/triflic anhydride (Tf2O) and the diphenylsulfoxide (Ph2SO)/Tf2O activator system. These sulfonium ion based activators proved to be efficient promoters for glycosylations in which inreactive (disarmed) 1-thioglycosides are employed. Furthermore, one-pot orthogonal and chemoselective oligosaccharide synthesis strategies that involve the use of 1-thioglycosides in combination with the above mentioned sulfonium based activator systems have proven to be feasible.

CarbohydratesGlycosylationsMonosaccharidesSulfoniumTEMPO-oxidationUronic Acids
Defense date
2007-04-18
Language
English
Supervisor(s)
Marel, G.A. van der; Overkleeft, H.S.
Qualification
Ph.D.
Degree granting institution
Faculty of Science, Leiden University, Leiden
Publisher
Leiden Institute of Chemistry/Bio-organic Synthesis, Faculty of Science, Leiden University
hdl
1887/12150

Funding

Sponsorship
Nederlandse Organisatie voor Wetenschappelijke Onderzoek Jurriaanse Stichting