Herein, we report the synthesis of calix[4]resorcinarene-based multivalent ligands bearing β-S-GlcNAc and β-S-AllNAc recognition elements. A clickable β-S-AllNAc derivative was successfully prepared from a β-thioalkynyl GlcNAc precursor, making profit of...
The syntheses of β-S-GlcA(13)GlcNAc and β-S-Gal(13)GlcNAc thiodisaccharides were achieved by SN2 displacement of a triflate group allocated at 3-position of a convenient 2-azido-4,6-O-benzylidene-2-deoxy-β-D-allopyranose precursor, by the corresponding nucleophilic suitable protected thioaldoses derived from GlcA and Gal.The study of the reaction led to the finding that the vinylazide formed by the competitive E2 reaction of the mentioned triflate, was an interesting precursor of a new kind of 2,3dideoxy-2-azido-(12) thiodisaccharides, through an addition reaction. The determination of the stereochemistry of the new stereocenter at C-2 was achieved by NOESY experiments. Final protecting group manipulation of the (13) thiodisaccharides led to a family of derivatives that could be used as building blocks for the synthesis of more complex glycomimetics.
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