Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides

Leendert J van den Bos; Jeroen D C Codée; John C van der Toorn; Thomas J Boltje; Jacques H van Boom; Herman S Overkleeft; Gijsbert A van der Marel

doi:10.1021/ol049380+

Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides

Org Lett. 2004 Jun 24;6(13):2165-8. doi: 10.1021/ol049380+.

Authors

Leendert J van den Bos¹, Jeroen D C Codée, John C van der Toorn, Thomas J Boltje, Jacques H van Boom, Herman S Overkleeft, Gijsbert A van der Marel

Affiliation

¹ Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.

PMID: 15200311
DOI: 10.1021/ol049380+

Abstract

[reaction: see text] Partially protected thioglycuronic acids are prepared efficiently by chemo- and regioselective oxidation of the corresponding thioglycosides using the TEMPO/BAIB reagent combination. After esterification, the thioglycuronic acids proved to be useful as both donor and acceptor in sulfonium-mediated condensations toward acidic di- and trisaccharides.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Cyclic N-Oxides
Glucuronides / chemical synthesis
Glucuronides / chemistry*
Glycosylation
Oxidation-Reduction
Sulfonium Compounds
Sulfur Compounds / chemical synthesis
Sulfur Compounds / chemistry*
Thioglycosides / chemistry
Trisaccharides / chemical synthesis*

Substances

Cyclic N-Oxides
Glucuronides
Sulfonium Compounds
Sulfur Compounds
Thioglycosides
Trisaccharides
TEMPO