ja046389y_si_002.cif (36.21 kB)
Synthesis of Postulated Molecular Probes: Stereoselective Free-Radical-Mediated C-Glycosylation in Tandem with Hydrogen Transfer
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posted on 2005-01-19, 00:00 authored by Yvan Guindon, Mohammed Bencheqroun, Abderrahim BouzideReported 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 (sLeX) 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 sLeX. In
this case, two 1,3-distant stereocenters were created with high diastereoselectivity using free radical
intermediates in a tandem process.