Synthesis of β-Cyclodextrin, Per-O-glycosylated through an Ethylene Glycol Spacer Arm

Abstract

The synthesis of cyclodextrin-based O-α-manno, O-β-galactopyranoside and O-β-galactofuranoside clusters, having seven sugar residues attached to the core, through ethylene, ethylenoxyethylene and ethylene-(dioxyethylene)-ethylene spacer arms is described. The synthesis involves the glycosylation of the oxyethylene arm and the attachment of the O-glycosides onto the heptakis(6-deoxy-6-iodo)-β-cyclodextrin derivative by means of nucleophilic displacement reaction using cesium carbonate in dimethylformamide.

Key words

carbohydrates - cyclodextrins - glycosylation - macrocycles - oligosaccharides

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