Cross metathesis for the synthesis of novel C-sialosides.
Cross metathesis of both anomers of C-allyl sialoside (3alpha/3beta) with styrene catalyzed by the second generation Grubbs or Hoveyda-Grubbs catalysts gave the corresponding aryl derivatives (4alpha/4beta) in virtually quantitative yields. The products were hydrogenated to model compounds 5alpha/5beta. Similarly, reaction of the alpha-anomer 3alpha with galactose derivative 8 gave the olefin-linked disaccharide mimetic 9. Following hydrogenation and deprotection, the ethylene-bridged Neu5Acalpha(2-->6)Gal analogue 11 could be obtained.
Meinke
Sebastian
S
University of Hamburg, Faculty of Science, Department of Chemistry, Hamburg, Germany.
Thiem
Joachim
J
D000498:Allyl Compounds / Q000737:chemistry; D002384:Catalysis; D006027:Glycosides / Q000138:chemical synthesis*; D019158:N-Acetylneuraminic Acid / Q000138:chemical synthesis*; D012428:Ruthenium / Q000737:chemistry*
D000498:Allyl Compounds; D006027:Glycosides; D012428:Ruthenium; D019158:N-Acetylneuraminic Acid