title: Thioglycuronides: synthesis and application in the assembly of acidic oligosaccharides.
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.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Leendert J
authors.initials: LJ
authors.lastname: van den Bos
authors.forename: Jeroen D C
authors.initials: JD
authors.lastname: Codée
authors.forename: John C
authors.initials: JC
authors.lastname: van der Toorn
authors.forename: Thomas J
authors.initials: TJ
authors.lastname: Boltje
authors.forename: Jacques H
authors.initials: JH
authors.lastname: van Boom
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
mesh_terms: D003497:Cyclic N-Oxides; D020719:Glucuronides / Q000138:chemical synthesis / Q000737:chemistry*; D006031:Glycosylation; D010084:Oxidation-Reduction; D013452:Sulfonium Compounds; D013457:Sulfur Compounds / Q000138:chemical synthesis / Q000737:chemistry*; D013865:Thioglycosides / Q000737:chemistry; D014312:Trisaccharides / Q000138:chemical synthesis*
chemical_list: D003497:Cyclic N-Oxides; D020719:Glucuronides; D013452:Sulfonium Compounds; D013457:Sulfur Compounds; D013865:Thioglycosides; D014312:Trisaccharides; C003959:TEMPO