Insertion of a D-glucosamine residue into the α-cyclodextrin skeleton; a model synthesis of ‘chimera cyclodextrins’

Abstract

Efficient conversion of α-cyclodextrin peracetate 2 into icosa-O-acetylmaltohexaose 3 by acetolytic fission of one glycosidic linkage, a series of manipulations including coupling with a 2-azido-2-deoxy-D-glucopyranose derivative, recyclization and final work-up (catalytic hydrogenolysis etc.) gave a novel β-cyclodextrin analogue 10 containing a D-glucosamine residue as a monosaccharide component.