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

Rapi, Zsolt and Ozohanics, Olivér and Tóth, Gábor and Bakó, Péter and Höfler, Lajos and Nemcsok, Tamás and Kánya, Zsolt and Keglevich, György (2016) Syntheses and complexing ability of α-d-gluco- and α-d-xylofuranoside-based lariat ethers. JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 85 (1). pp. 19-32. ISSN 1388-3127, (eISSN: 1573-1111)

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Abstract

Chiral monoaza-15-crown-5 lariat ethers attached to a 1,2-O-izopropilidene-α-d-glucofuranoside unit (10-13), monoaza-16-crown-5 lariat ethers fused to 1,2-O-izopropilidene-α-d-glucofuranoside- (18) and 1,2-O-isopropylidene-α-d-xylofuranoside units (23, 24) have been synthesized. The alkali metal- and ammonium picrate extracting ability of a few macrocycles was investigated in dichloromethane – water system. It can be seen that, in general the 15-membered macrocycles (10-13) show, for almost all cations, a bigger extracting ability than the 16-membered lariat ethers (18, 23, 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-izopropilidene-α-d-glucofuranoside based lariat ethers (13) exhibited a high selectivity for silver ion (Ag+).

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