Coupling of N-tosylhydrazones with tetrazoles: synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics?

Organic & Biomolecular Chemistry Pub Date: 2020-12-21 DOI: 10.1039/D0OB02248A

Abstract

Coupling reactions of O-peracylated 2,6-anhydro-aldose tosylhydrazones (C-(β-D-glycopyranosyl)formaldehyde tosylhydrazones) with tetrazoles were studied under metal-free conditions using thermic or microwave activation in the presence of different bases. The reactions proved highly regioselective and gave the corresponding, up-to-now unknown 2-β-D-glycopyranosylmethyl-2H-tetrazoles in 7–67% yields. The method can be applied to get new types of disaccharide mimetics, 5-glycosyl-2-glycopyranosylmethyl-2H-tetrazoles, as well. Galectin binding studies with C-(β-D-galactopyranosyl)formaldehyde tosylhydrazone and 2-(β-D-galactopyranosylmethyl)-5-phenyl-2H-tetrazole revealed no significant inhibition of any of these lectins.

Graphical abstract: Coupling of N-tosylhydrazones with tetrazoles: synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics
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