title: Sequential one-pot glycosylations using 1-hydroxyl and 1-thiodonors.
abstract: [reaction: see text] A novel sequential glycosylation procedure is described that combines the use of 1-hydroxyl and thiodonors. The Ph(2)SO/Tf(2)O-mediated dehydrative condensation of 1-hydroxyl donors with thioglycosides affords in good yield the thiodisaccharides, which in turn can be activated by the same activator system to furnish trisaccharides. The alpha-Gal epitope and a hyaluronan trisaccharide were efficiently assembled in a one-pot procedure.
authors.affiliation: Leiden Institute of Chemistry, Leiden University, P.O. Box 9502, 2300 RA Leiden, The Netherlands.
authors.forename: Jeroen D C
authors.initials: JD
authors.lastname: Codée
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: Herman S
authors.initials: HS
authors.lastname: Overkleeft
authors.forename: Jacques H
authors.initials: JH
authors.lastname: van Boom
authors.forename: Gijs A
authors.initials: GA
authors.lastname: van der Marel
mesh_terms: D002240:Carbohydrate Sequence; D006031:Glycosylation; D007202:Indicators and Reagents; D008969:Molecular Sequence Data; D014312:Trisaccharides / Q000138:chemical synthesis*
chemical_list: D007202:Indicators and Reagents; D014312:Trisaccharides