Aryl-C-glycosides are compounds resistant to acidic and enzymatic hydrolysis. These compounds find application in biochemistry and pharmacochemistry as synthetic lectin ligands. Thanks to affinity to these receptors, they are used and tested in anti-adhesion therapy.
In this work, we describe the synthesis of new non-hydrolyzable aryl-C-glycosides by Pd-catalysed cross-coupling reaction of L-fuco pinacol boronate with electron rich arylhalogenides. The advantage of this approach is a highly stereoselective oxidative-reductive transformation of aryl-C-glycosides with L-fuco configuration. Several β-aryl-C-glycosides were prepared by this transformation in good yields. The target molecules will be tested for their interaction with bacterial lectines.
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