title: DISAL glycosyl donors for the synthesis of a linear hexasaccharide under mild conditions.
abstract: [reaction: see text] The new class of glycosyl donors with a methyl 3,5-dinitrosalicylate (DISAL) anomeric leaving group has proved efficient for glycosylation under strictly neutral, mildly basic, or mildly acidic conditions. Here, we report the synthesis of novel DISAL disaccharide glycosyl donors prepared by easy nucleophilic aromatic substitution. These DISAL donors proved efficient in the synthesis of a starch-related hexasaccharide under very mild conditions. Glycosylations proceeded with alpha-selectivity and were compatible with Trt protecting groups.
authors.affiliation: Department of Chemistry, Technical University of Denmark, Building 201, Kemitorvet, DK-2800 Kgs. Lyngby, Denmark.
authors.forename: Lars
authors.initials: L
authors.lastname: Petersen
authors.forename: Jane B
authors.initials: JB
authors.lastname: Laursen
authors.forename: Kim
authors.initials: K
authors.lastname: Larsen
authors.forename: M Saddik
authors.initials: MS
authors.lastname: Motawia
authors.forename: Knud J
authors.initials: KJ
authors.lastname: Jensen
mesh_terms: D002240:Carbohydrate Sequence; D003511:Cyclohexanols / Q000737:chemistry; D006027:Glycosides / Q000138:chemical synthesis*; D006031:Glycosylation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D012459:Salicylates / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D003511:Cyclohexanols; D006027:Glycosides; D009844:Oligosaccharides; D012459:Salicylates