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Updated: Jun 9, 2026

Chemoselective Modification of Viral Surfaces via Bioorthogonal Click Chemistry
Published on: August 19, 2012
Synthesis of postulated molecular probes: stereoselective free-radical-mediated C-glycosylation in tandem with
Yvan Guindon1, Mohammed Bencheqroun, Abderrahim Bouzide
1Bio-organic Chemistry Laboratory, Institut de recherches cliniques de Montréal (IRCM), 110 avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7. guindoy@ircm.qc.ca
Abstract:
Reported herein is a strategy employing an addition reaction in tandem with a hydrogen-transfer reaction for the elaboration of C-glycoside-based sialyl Lewis X (sLe(X)) analogues. Significant stereocontrol was noted when alkyl radicals were reacted with a series of alkoxytaconates. Transition states were proposed to explain the obtained selectivity. Further reaction between an anomeric-centered fucosyl-derived radical and a galactosylated hydroxytaconate provided easy access to C,O-diglycosides as mimics of sLe(X). In this case, two 1,3-distant stereocenters were created with high diastereoselectivity using free radical intermediates in a tandem process.
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