title: A simple access to lactose-derived building blocks required in glycoconjugate synthesis.
abstract: Lactose was readily transformed into thexyldimethylsilyl (3,4-O-isopropylidene-beta-D-galactopyranosyl)-(1-->4)-beta- D-glucopyranoside (5); this compound served as intermediate for the generation of partially O-protected lactose building blocks required in oligosaccharide and glycoconjugate synthesis. Thus, from 5 via per-O-benzoylation, desilylation, trichloroacetimidate formation, glycosylation of the Lemieux spacer, and acid-catalyzed de-O-isopropylidenation methoxycarbonyloctyl (2,6-di-O-benzoyl-beta-D-galactopyranosyl)- (1-->4)-2,3,6-tri-O-benzoyl-beta-D-glucopyranoside (12) was obtained. Regioselective benzoylation of 5 with benzoyl cyanide under various conditions afforded 3-O- (13), 2,3,2'-O- (14), 3,2'-O- (16), and 2,2'-O-unprotected (17) lactoside, respectively. De-O-isopropylidenation of 16 gave thexyldimethylsilyl (6-O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-2, 6-di-O-benzoyl-beta-D-glucopyranoside (18), an important 2',3',4'-O-unprotected lactose derivative. Fucosylation of 13 and then de-O-isopropylidenation afforded thexyldimethylsilyl 2,6-di-O-benzoyl-beta-D-galactopyranosyl)-(1-->4)-[(3,4-di-O-acetyl-2-O- benzoyl-alpha-L-fucopyranosyl)-(1-->3)]-2,6-di-O-benzoyl-beta-D- glucopyranoside (21), an important fucosyllactose building block.
authors.affiliation: Fakultät für Chemie, Universität Konstanz, Germany.
authors.forename: L
authors.initials: L
authors.lastname: Lay
authors.forename: R
authors.initials: R
authors.lastname: Windmüller
authors.forename: S
authors.initials: S
authors.lastname: Reinhardt
authors.forename: R R
authors.initials: RR
authors.lastname: Schmidt
mesh_terms: D002240:Carbohydrate Sequence; D006001:Glycoconjugates / Q000138:chemical synthesis*; D007785:Lactose / Q000737:chemistry*; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*
chemical_list: D006001:Glycoconjugates; D009844:Oligosaccharides; D007785:Lactose