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Synthesis 2001(7): 1057-1064
DOI: 10.1055/s-2001-14574
PAPER
© Georg Thieme Verlag Stuttgart · New York

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

Africa García-Barrientosa, Juan J. García-Lópezb, Joaquín Isac-Garcíaa, Fernando Ortega-Caballerob, Clara Uriela, Antonio Vargas-Berenguel*b, Francisco Santoyo-González*a
a Instituto de Biotecnología, Facultad de Ciencias, Universidad de Granada, 18071 Granada, Spain
b Área de Química Orgánica, Universidad de Almería, 04120 Almería, Spain
Fax: +34-958243186; +34-950015481; e-Mail: fsantoyo@ugr.es; avargas@ual.es;
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Publication History

Received 26 January 2001
Publication Date:
30 September 2004 (online)

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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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