title: Preparation of 1-thio uronic acid lactones and their use in oligosaccharide synthesis.
abstract: The chemo- and regioselective TEMPO/BAIB-mediated oxidation of 2,6- and 3,6-dihydroxy 1-thio glycopyranosides to the corresponding 1-thio uronic acid lactones is described. These locked 1-thio glycuronides can directly be used as donors in glycosidation reactions using the Ph(2)SO/Tf(2)O reagent system. Alternatively, selective opening of the lactone bridge liberates a hydroxyl function for ensuing glycosylations.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, The Netherlands.
authors.forename: Leendert J
authors.initials: LJ
authors.lastname: van den Bos
authors.forename: Remy E J N
authors.initials: RE
authors.lastname: Litjens
authors.forename: Richard J B H N
authors.initials: RJ
authors.lastname: van den Berg
authors.forename: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Gijsbert A
authors.initials: GA
authors.lastname: van der Marel
mesh_terms: D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D013237:Stereoisomerism; D014574:Uronic Acids / Q000138:chemical synthesis*
chemical_list: D007783:Lactones; D009844:Oligosaccharides; D014574:Uronic Acids