title: Palladium-charcoal-catalyzed reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide: a route to small cluster oligosaccharide mimetics (SCOMs).
abstract: [reaction: see text] Synthesis of glycosyl cyanides was optimized with a new catalyst system. Reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide with Pd-hydrogen, in the presence of Ac(2)O and Boc(2)O, gave N-protected-mono- and -di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl)-amines, which allow for the syntheses of small cluster oligosaccharide mimetics of fucopyranosylomethyl-substituted ureas. From di-(2,3,4-tri-O-acetyl-beta-L-fucopyranosylmethyl) amine was also prepared a carbamoyl chloride as a potentially useful synthon for preparation of more complex C-glycosidic conjugates.
authors.affiliation: Department of Chemistry, University of the Pacific, 3601 Pacific Avenue, Stockton, California 95211, USA.
authors.forename: Pasit
authors.initials: P
authors.lastname: Phiasivongsa
authors.forename: Julie
authors.initials: J
authors.lastname: Gallagher
authors.forename: Chang-Nan
authors.initials: CN
authors.lastname: Chen
authors.forename: Patrick R
authors.initials: PR
authors.lastname: Jones
authors.forename: Vyacheslav V
authors.initials: VV
authors.lastname: Samoshin
authors.forename: Paul H
authors.initials: PH
authors.lastname: Gross
mesh_terms: D002384:Catalysis; D002606:Charcoal / Q000737:chemistry; D003486:Cyanides / Q000737:chemistry; D005643:Fucose / Q000737:chemistry*; D018716:Molecular Mimicry; D009844:Oligosaccharides / Q000138:chemical synthesis*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry
chemical_list: D003486:Cyanides; D009844:Oligosaccharides; D002606:Charcoal; D005643:Fucose; D010165:Palladium