title: Side reactions with 2,2,2-trichloroethoxysulfates during the synthesis of glycans.
abstract: Protected sulfate groups may be used as an alternative tool to provide sulfate esters at hydroxyl and amino groups, particularly on complex glycans. We examined 2,2,2-trichloroethoxysulfation at the mono-, di-, and trihydroxyl groups of saccharide moieties to show regioselective sulfation. We found some side reactions including inter- and intramolecular nucleophilic reactions with 2,2,2-trichloroethoxysulfates.
authors.affiliation: Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyamacho-Minami, Tottori 680-8552, Japan.
authors.forename: Kenya
authors.initials: K
authors.lastname: Matsushita
authors.affiliation: Otsuka Chemical Co, Ltd, 463 Kagasuno, Kawauchi-cho, Tokushima 771-0193, Japan.
authors.forename: Yuta
authors.initials: Y
authors.lastname: Sato
authors.affiliation: Department of Regional Environment, Faculty of Regional Sciences, Tottori University, 4-101 Koyamacho-Minami, Tottori 680-8551, Japan.
authors.forename: Shinji
authors.initials: S
authors.lastname: Funamoto
authors.affiliation: Department of Chemistry and Biotechnology, Graduate School of Engineering, Tottori University, 4-101 Koyamacho-Minami, Tottori 680-8552, Japan; Department of Regional Environment, Faculty of Regional Sciences, Tottori University, 4-101 Koyamacho-Minami, Tottori 680-8551, Japan. Electronic address: jtamura@rs.tottori-u.ac.jp.
authors.forename: Jun-ichi
authors.initials: J
authors.lastname: Tamura
mesh_terms: D002236:Carbohydrate Conformation; D018360:Crystallography, X-Ray; D008958:Models, Molecular; D011134:Polysaccharides / Q000138:chemical synthesis*; D013431:Sulfates / Q000737:chemistry*
chemical_list: D011134:Polysaccharides; D013431:Sulfates
keywords: 2,2,2-Trichloroethoxysulfate; Glycan synthesis; Intramolecular attack; Protected sulfate; Sulfated oligosaccharide