844867-20-5Relevant articles and documents
Synthesis of postulated molecular probes: Stereoselective free-radical-mediated C-glycosylation in tandem with hydrogen transfer
Guindon, Yvan,Bencheqroun, Mohammed,Bouzide, Abderrahim
, p. 554 - 558 (2005)
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 (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.
