Palladium-charcoal-catalyzed reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide: a route to small cluster oligosaccharide mimetics (SCOMs).
[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.
Phiasivongsa
Pasit
P
Department of Chemistry, University of the Pacific, 3601 Pacific Avenue, Stockton, California 95211, USA.
Gallagher
Julie
J
Chen
Chang-Nan
CN
Jones
Patrick R
PR
Samoshin
Vyacheslav V
VV
Gross
Paul H
PH
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
D003486:Cyanides; D009844:Oligosaccharides; D002606:Charcoal; D005643:Fucose; D010165:Palladium