Calix[8]arene-based glycoconjugates as multivalent carbohydrate-presenting systems

An efficient approach for the introduction of eight mono- or disaccharide sugar moieties (d-glucose, N-acetyl-d-glucosamine, d-galactose, l-fucose, d-maltose and d-cellobiose) at the upper rim of calix[8]arene 1, using thioureido linkers, is reported. The obtained water-soluble, nanosized glycocalix[8]arenes 5b–10b may act as biomimetic carbohydrate systems and as hosts for highly polar organic molecules. Preliminary 1H NMR complexation experiments of octaglycosyl derivative 7b and 10b with ionic guests are also reported.