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Synthesis 2007(14): 2186-2192  
DOI: 10.1055/s-2007-983753
PAPER
© Georg Thieme Verlag Stuttgart · New York

Expeditious Synthesis of Glycosylated Phthalocyanines

Xavier Álvarez-Micó, Mario J. F. Calvete, Michael Hanack, Thomas Ziegler*
Institute of Organic Chemistry, University of Tuebingen, Auf der Morgenstelle 18, 72076 Tuebingen, Germany
Fax: +49(7071)295244; e-Mail: thomas.ziegler@uni-tuebingen.de;
Further Information

Publication History

Received 23 February 2007
Publication Date:
03 July 2007 (online)

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Abstract

3,4-Dicyanophenyl O- and S-glycosides in the gluco, galacto, lacto, and cellobiose series were prepared in virtually quantitative yield through nucleophilic aromatic substitution of 4-nitrophthalonitrile with acetyl-protected glycoses and 1-thio-glycoses. Similarly, 2-(3,4-dicyanophenoxy)ethyl 2,3,4,6-tetra-O-acetyl-β-d-gluco- and galacto-pyranosides were obtained by nucleophilic substitution of 2-(tosyloxy)ethyl 2,3,4,6-tetra-O-acetyl-β-d-gluco- and -galactopyranoside with 3,4-dicyanophenol in 82% and 94% yields, respectively. All glycosides were deacetylated and tetramerized to the corresponding glycosylated zinc(II) phthalocyanines without further purification using a template condensation in 42-54% yields.

Key words

carbohydrate - phthalocyanine - glycoside - cellular uptake

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