Convenient Synthesis of a Galacturonic Acid Based Macrocycle with Potential Copper‐Complexation Ability

Abstract

Abstract A convenient approach to the construction of a galacturonic acid based macrocycle containing an amide group and a triazole ring has been achieved. The key step relies on the efficient formation of a 16‐membered ring by a copper‐catalysed intramolecular cycloaddition reaction applied to analkyne‐azide galacturonate. Depending on the reaction conditions, the outcome of the 1,3‐dipolar cycloaddition varied; the expected intramolecular 1,4‐triazole was obtained as well as a C 2 ‐symmetric dimer in different ratios. A preliminary study of the complexation properties of this macrocycle towards Cu II cations revealed the formation of cryptates in a 1:1 metal/ligand ratio.