Synthesis of the C-glycoside analogue of a novel sialyl Lewis X mimetic.
Sialyl Lewis X (sLex) mimetics that can function as selectin antagonists have received considerable attention in connection with the development of novel antiinflammatory therapies. An interesting structure that emerged from the studies of the Wong group is the 1,1-Gal-Man disaccharide 2, reported to bind E-selectin 5 times more strongly than sLex. The C-glycoside derivative 3 is of interest both as a conformational probe for selectin binding and as a hydrolytically stable analogue. Herein we illustrate a novel methodology for beta-C-galacto-disaccharides in the synthesis of 3. The protocol has as a key step a novel oxocarbenium ion-enol ether cyclization to give a C1-substituted galactal.
Cheng
X
X
Department of Chemistry, Hunter College/CUNY, New York 10021, USA.
Khan
N
N
Mootoo
D R
DR
D000894:Anti-Inflammatory Agents, Non-Steroidal / Q000138:chemical synthesis*; D002240:Carbohydrate Sequence; D006027:Glycosides / Q000138:chemical synthesis; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D008969:Molecular Sequence Data; D009844:Oligosaccharides / Q000138:chemical synthesis*; D017452:Receptors, IgG / Q000737:chemistry*; D000080506:Sialyl Lewis X Antigen; D016339:Spectrometry, Mass, Fast Atom Bombardment
D000894:Anti-Inflammatory Agents, Non-Steroidal; D006027:Glycosides; D009844:Oligosaccharides; D017452:Receptors, IgG; D000080506:Sialyl Lewis X Antigen