Synthesis of a potent antagonist of E-selectin.
A synthesis of an antagonist of E-selectin previously reported by a group at Novartis Pharma in Basel is described. An important feature involves the formation of an ether linkage based on a Rh(II)-catalyzed reaction. Stereocontrolled glycosylations rely on the anomeric activation of 2-pyridylthio carbonate as leaving group for the attachment of beta-D-galactopyranosyl and alpha-L-fucopyranosyl units on a common 1,5-anhydro D-glucitol scaffold.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montréal, Québec H3C 3J7 Canada. stephen.hanessian@umontreal.ca
Mascitti
Vincent
V
Rogel
Olivier
O
D002384:Catalysis; D002625:Chemistry, Organic / Q000379:methods; D003500:Cyclization; D019040:E-Selectin; D005960:Glucosides / Q000138:chemical synthesis*; D006031:Glycosylation; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D012238:Rhodium; D013237:Stereoisomerism
D019040:E-Selectin; D005960:Glucosides; D012238:Rhodium