Synthesis of Aryl-C-Glycosides Derived from L-Fucose

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Mini symposium: Glycobiology at the LUMC and beyond

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Synthesis of Aryl-C-Glycosides Derived from L-Fucose

Vít Prouza 1 , Parkan Kamil 1

1 UCT Prague, Prague, Czech Republic

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.[1]

In this work, we describe the synthesis of new non-hydrolyzable aryl-C-glycosides by Pd-catalysed cross-coupling reaction[2] 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.[1]

synthesis of aryl-C-glycosides

Ofek, I.; Hasty, D. L.; Sharon, N., Anti-adhesion therapy of bacterial diseases: prospects and problems. FEMS Immunol. Med. Microbiol. 2003, 38 (3), 181-191.

Parkan, K.; Pohl, R.; Kotora, M., Cross-Coupling Reaction of Saccharide-Based Alkenyl Boronic Acids with Aryl Halides: The Synthesis of Bergenin. Chem. - Eur. J. 2014, 20 (15), 4414-4419.

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