New β-cyclodextrin derivatives possessing biologically active saccharide antennae

Abstract

The synthesis of monosubstituted β-cyclodextrin derivatives having the monosaccharides, β-D-glucose, β-D-galactose, α-D-mannose, β-L and β-D-fucose linked to the macrocycle via a C9 spacer chain is described. The approach is based on the highly efficient coupling of the NCS sugar derivatives to monomethyl nonanedicarboxylate to generate a stable amido linkage. The NMR studies show the saccharide antennae to be oriented into the environment and not towards the CD cavity.