Synthesis of a 20-Crown-6 from D-Glucose and First Study of its Alkali Metal Cations Affinity by MALDI-FTMS

For many years now, some of us have been involved in synthesizing various crown ethers from suitably protected hexopyranosides [1,2] or D-mannitol frameworks [3,4]. We report here the synthesis of a novel macrocycle from D-glucose incorporating a flexible biphenyl unit and a primary amine function at C-6 on the sugar moiety and some of its complexing abilities towards various guests, examined for the first time by Matrix Assisted Laser Desorption Ionization with Fourier Transform Mass Spectrometry (MALDI-FTMS).