Synthesis of Novel Bis-Triazolyl Glycoconjugates via Dual Click Reaction for the Selective Recognition of Cu(II) Ions

Abstract

Glycosyl-β-azidoester, obtained from corresponding olefinic ester via one-pot tandem Michael-diazotransfer reaction, on click coupling with di-O-propargylated ethers afforded high yields of novel bis-triazolyl glycoconjugates. The resulting two distinct class of bis-triazolyl glycoconjugates includes the bidentate 3-O-protected-α-D-glucofuranose bearing two triazolyl glycosylated-β-triazoloester groups at 5,6-positions of sugar scaffold and 1,4:3,6-dianhydro-D-mannitol-based bidentate glycoconjugate with two triazole groups at 2,5 position of sugar scaffold (S1), and all the triazolyl glycoconjugates been characterization using standard spectral analysis. One of the developed bis-triazolyl glycoconjugate 7 a has sucessfully been explored as a promissing sensor for the selective recognition of Cu2+ ions. The probe S1 displayed moderate selective detection of Cu2+ ions by means of ultraviolet spectroscopy. The Job plot experiment suggested 1:1 complexation of probe S1 (compound 7 a) with Cu2+ ions having a detection limit of 8.00 μM.