N-Glycosylamines of 4,6-Oethylidene-α-D-gIucopyranose: Synthesis, characterisation and structure of CO2H, Cl and F ortho-substituted phenyl derivatives and metal ion complexes of the CO2H derivative

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N-Glycosylamines of 4,6-Oethylidene-α-D-gIucopyranose: Synthesis, characterisation and structure of CO2H, Cl and F ortho-substituted phenyl derivatives and metal ion complexes of the CO2H derivative

Year : 2000

Source Title : Journal of the Chemical Society, Dalton Transactions

Document Type :

Abstract

A saccharide based ligand suitable for metal binding (HLCOOH) has been synthesized using 4,6-O-ethylidene-α-D-glucopyranose (4,6-O-EGP) and anthranilic acid. A few analogous glycosylamines with chloro and fluoro ortho substitutions have also been synthesized and characterised. Complexes of HLCOOHwith Na+, K+, Mg2+, Ca2+, Ba2+, Cd2+ and Hg2+ have been isolated and characterised fully. The crystal structures of 4,6-O-EGP, the chloro analogue of HLCOOH and the K+ complex of LCOOH are established. The anomeric nature, orientation of the binding core and the co-ordination aspects of K+ have been derived from these structures. ©The Royal Society of Chemistry 2000.