title: Large-scale synthesis of 6-deoxy-6-sulfonatomethyl glycosides and their application for novel synthesis of a heparinoid pentasaccharide trisulfonic acid of anticoagulant activity.
abstract: Multigram-scale syntheses of three 6-deoxy-6-sulfonatomethyl α-glucosides were accomplished via reactions of the corresponding primary triflate derivatives with the lithiated ethyl methanesulfonate. Chemoselective glycosylation reactions of different 6-C-sulfonatomethyl glucoside donors were studied. The sulfonic acid-containing building blocks were utilised in a novel [2+3] block synthesis of a trisulfonic acid isoster of the anticoagulant pentasaccharide idraparinux.
authors.affiliation: Department of Pharmaceutical Chemistry, Medical and Health Science Center, University of Debrecen, PO Box 70, H-4010 Debrecen, Hungary; Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary.
authors.forename: Erika
authors.initials: E
authors.lastname: Mező
authors.affiliation: Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary.
authors.forename: Mihály
authors.initials: M
authors.lastname: Herczeg
authors.affiliation: Department of Pharmaceutical Chemistry, Medical and Health Science Center, University of Debrecen, PO Box 70, H-4010 Debrecen, Hungary; Department of Organic Chemistry, University of Debrecen, PO Box 20, H-4010 Debrecen, Hungary.
authors.forename: Dániel
authors.initials: D
authors.lastname: Eszenyi
authors.affiliation: Department of Pharmaceutical Chemistry, Medical and Health Science Center, University of Debrecen, PO Box 70, H-4010 Debrecen, Hungary. Electronic address: borbas.aniko@pharm.unideb.hu.
authors.forename: Anikó
authors.initials: A
authors.lastname: Borbás
mesh_terms: D000925:Anticoagulants / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D006496:Heparinoids / Q000138:chemical synthesis*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D013451:Sulfonic Acids / Q000138:chemical synthesis*; D014574:Uronic Acids / Q000737:chemistry
chemical_list: D000925:Anticoagulants; D006027:Glycosides; D006496:Heparinoids; D009844:Oligosaccharides; D013451:Sulfonic Acids; D014574:Uronic Acids
keywords: Aglycon transfer; Anticoagulation; Chemoselective glycosylation; Pentasaccharide; Sulfonic acid; Uronic acids