Palladium-charcoal-catalyzed reduction of tri-O-acetyl-beta-L-fucopyranosyl cyanide: a route to small cluster oligosaccharide mimetics (SCOMs)

Org Lett. 2002 Dec 26;4(26):4587-90. doi: 10.1021/ol020123j.

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Charcoal / chemistry
  • Cyanides / chemistry
  • Fucose / chemistry*
  • Molecular Mimicry*
  • Oligosaccharides / chemical synthesis*
  • Oxidation-Reduction
  • Palladium / chemistry

Substances

  • Cyanides
  • Oligosaccharides
  • Charcoal
  • Fucose
  • Palladium