Syntheses and complexing ability of α-d-gluco- and α-d-xylofuranoside-based lariat ethers

Abstract

Chiral monoaza-15-crown-5 lariat ethers attached to a 1,2-O-isopropylidene-α-d-glucofuranoside unit (10–13), monoaza-16-crown-5 lariat ethers fused to 1,2-O-isopropylidene-α-d-glucofuranoside- (18) and to 1,2-O-isopropylidene-α-d-xylofuranoside units (23 and 24) have been synthesized. The alkali metal- and ammonium picrate extracting ability of these macrocycles was investigated in dichloromethane–water system. In general, the 15-membered macrocycles (10–13) showed, for almost all cations, a more considerable extracting ability, than the 16-membered lariat ethers (18, 23 and 24). Plasticized PVC membrane electrodes (ISEs) were prepared from the α-d-glucofuranoside-based triphenylmetyl (trityl) ether derivative (18), and its potentiometric selectivities and complex formation constants were determined with the segmented sandwich membrane method. Furthermore, the binding affinities of ionophores to different metal ions were also measured by competitive ESI–MS experiments. One of the 1,2-O-isopropylidene-α-d-glucofuranoside-based lariat ethers (13) exhibited a high selectivity for silver ion (Ag+).