Download PDF
Synthesis 2010(18): 3097-3104  
DOI: 10.1055/s-0030-1258178
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of Octaglycosylated Zinc(II) Phthalocyanines

Zafar Iqbala, Alexey Lyubimtseva,b, Timo Herrmannc, Michael Hanack*a, Thomas Ziegler*a
a Institut für Organische Chemie, Universität Tübingen, Auf der Morgenstelle 18, 72076 Tübingen, Germany
Fax: +49(7071)295268; e-Mail: hanack@uni-tuebingen.de ; e-Mail: thomas.ziegler@uni-tuebingen.de;
b Ivanovo State University of Chemistry and Technology, Organic Chemistry Department, F. Engels Str. 7, 153460 Ivanovo, Russian Federation
c Medical and Natural Sciences Research Centre, Universität Tübingen, Ob dem Himmelreich 7, 72074 Tübingen, Germany
Further Information

Publication History

Received 24 March 2010
Publication Date:
16 July 2010 (online)

    Permissions and Reprints All articles of this category

Abstract

For the first time, octaglycosylated zinc(II) phthalocyanines in which the sugar part is protected by acetyl groups and the deprotected zinc(II) phthalocyanines were synthesized and characterized. The sugars glucose, galactose, lactose, cellobiose, and maltose are anomerically attached either via oxygen or sulfur to the phthalocyanine ring. The necessary starting materials for the syntheses of the phthalocyanines, the anomerically 4,5-diglycosylated phthalonitriles, were obtained by reacting the anomerically deprotected sugars containing OH and SH groups with 4,5-difluorophthalonitrile. The acetyl protected octaglycosylated phthalocyanines were obtained in yields between 55 and 78% by heating the anomerically 4,5-diglycosylated phthalonitriles in DMF with hexamethyldisilazane, p-toluenesulfonic acid, and zinc acetate. The acetyl groups in sugar moieties were removed to afford corresponding water­-soluble phthalocyanines.

Key words

phthalocyanines - octaglycosylated - zinc - structural isomers

    References

  • 1 Alvarez-Mico X. Calvete MJF. Hanack M. Ziegler T. Tetrahedron Lett.  2006,  47:  3283 
    CrossrefGoogle Scholar
  • 2 Alvarez-Mico X. Calvete MJF. Hanack M. Ziegler T. Synthesis  2007,  2186 
    Article in Thieme ConnectGoogle Scholar
  • 3a Choi C.-F. Huang J.-D. Lo P.-C. Fong W.-P. Ng DKP. Org. Biomol. Chem.  2008,  6:  2173 
    Google Scholar
  • 3b Lo P.-C. Chan CMH. Liu J.-Y. Fong W.-P. Ng DKP. J. Med. Chem.  2007,  50:  2100 
    Google Scholar
  • 3c Reddy RM. Shibata N. Yoshiyama H. Nakamura S. Toru T. Synlett  2007,  628 
    Google Scholar
  • 3d Soares ARM. Tome JPC. Neves MGPMS. Tome AC. Cavaleiro JAS. Torres T. Carbohydr. Res.  2009,  344:  507 
    Google Scholar
  • 3e Ribeiro AO. Tome JPC. Neves MGPMS. Tome AC. Cavaleiro JAS. Iamamoto Y. Torres T. Tetrahedron Lett.  2006,  47:  9177 
    Google Scholar
  • 3f Kumru U. Ermeydan MA. Dumoulin F. Ahsen V. J. Porphyrins Phthalocyanines  2008,  12:  1090 
    Google Scholar
  • 3g Lee PPS. Lo P.-C. Chan EYM. Fong W.-P. Ko W.-H. Ng DKP. Tetrahedron Lett.  2005,  46:  1551 
    Google Scholar
  • 3h Zorlu Y. Ermeydan MA. Dumoulin F. Ahsen V. Savoie H. Boyle RS. Photochem. Photobiol. Sci.  2009,  8:  312 
    Google Scholar
  • 4 Alvarez-Mico X. Calvete MJF. Hanack M. Ziegler T. Carbohydr. Res.  2007,  342:  440 
    CrossrefGoogle Scholar
  • 5 Schmid G. Sommerauer M. Geyer M. Hanack M. In Phthalocyanines: Properties and Applications   Vol. 4:  Leznoff CC. Lever ABP. VCH; Weinheim: 1996.  p.1-18  
    Google Scholar
  • 6 Iqbal Z. Hanack M. Ziegler T. Tetrahedron Lett.  2009,  50:  873 
    CrossrefGoogle Scholar
  • 7 Ohle H. Behrend G. Ber. Dtsch. Chem. Ges.  1925,  58:  2585 
    CrossrefGoogle Scholar
  • 8 Uchida H. Tanaka H. Yoshiyama H. Reddy PY. Nakamura S. Toru T. Synlett  2002,  1649 
    Article in Thieme ConnectGoogle Scholar
  • 9 Uchida H. Yoshiyama H. Reddy PY. Nakamura S. Toru T. Bull. Chem. Soc. Jpn.  2004,  77:  1401 
    CrossrefGoogle Scholar