title: A simple synthesis of 8-(methoxycarbonyl)octyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside and derivatives and their use in the preparation of neoglycoconjugates.
abstract: 8-(Methoxycarbonyl)octyl 3,6-di-O-(alpha-D-mannopyranosyl)-alpha-D-mannopyranoside (10) was synthesized in 54% yield by regioselective diglycosylation of unprotected mannoside 4, employing the trichloroacetimidate donor 1, followed by debenzoylation. Derivatives of compounds 4 and 10 were used to prepare conjugates containing fluorochromes for the study of carbohydrate-lectin interactions, as well as conjugates with phospholipids for the preparation of liposomes.
authors.affiliation: Industrial Research Ltd, Lower Hutt, New Zealand.
authors.forename: B
authors.initials: B
authors.lastname: Becker
authors.forename: R H
authors.initials: RH
authors.lastname: Furneaux
authors.forename: F
authors.initials: F
authors.lastname: Reck
authors.forename: O A
authors.initials: OA
authors.lastname: Zubkov
mesh_terms: D002240:Carbohydrate Sequence; D004187:Disaccharides / Q000138:chemical synthesis*; D006001:Glycoconjugates / Q000138:chemical synthesis*; D008362:Mannosides / Q000138:chemical synthesis*; D008969:Molecular Sequence Data
chemical_list: C120598:8-(methoxycarbonyl)octyl 3,6-di-O-(mannopyranosyl)-mannopyranoside; D004187:Disaccharides; D006001:Glycoconjugates; D008362:Mannosides