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Synthesis of a potent antagonist of E-selectin
Stephen Hanessian1, Vincent Mascitti, Olivier Rogel
1Department of Chemistry, Université de Montréal, C.P. 6128, Succursale Centre-ville, Montréal, Québec H3C 3J7 Canada. stephen.hanessian@umontreal.ca
The Journal of Organic Chemistry
|May 11, 2002
Abstract:
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.