title: D-galacturonic acid derivatives as acceptors and donors in glycosylation reactions.
abstract: Jones oxidation of suitably protected allyl beta-D-galactopyranosides and subsequent esterification were reinvestigated. Partial deprotection of the resulting D-galacturonic acid derivatives afforded compounds suitable for transformation into glycosyl acceptors. The synthesis of 2-, 3-, and 4-trityl ethers, relying on efficient differential protecting-group strategies, is described. Trityl-cyanoethylidene condensation of these trityl ethers, leading to the protected disaccharide units beta-D-GalpA-(1-->2)-D-GalpA and beta-D-GalpA-(1-->3)-GalpA with high stereoselectivity, is demonstrated. A beta-D-GalpA-(1-->4)-D-GalpA disaccharide was also prepared.
authors.affiliation: Universität Rostock, Fachbereich Chemie, Germany.
authors.forename: C
authors.initials: C
authors.lastname: Vogel
authors.forename: W
authors.initials: W
authors.lastname: Steffan
authors.lastname: Ott AYa
authors.forename: V I
authors.initials: VI
authors.lastname: Betaneli
mesh_terms: D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D005697:Galactosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006603:Hexuronic Acids / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D008969:Molecular Sequence Data
chemical_list: D004187:Disaccharides; D005697:Galactosides; D006603:Hexuronic Acids; C007819:galacturonic acid