Synthesis of postulated molecular probes: stereoselective free-radical-mediated C-glycosylation in tandem with hydrogen transfer |
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Authors: | Guindon Yvan Bencheqroun Mohammed Bouzide Abderrahim |
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Institution: | Bio-organic Chemistry Laboratory, Institut de recherches cliniques de Montréal (IRCM), 110 avenue des Pins Ouest, Montréal, Québec, Canada H2W 1R7. guindoy@ircm.qc.ca |
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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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