ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

Synthesis of ether-linked [60]fullerene glycoconjugates by nucleophilic cyclopropanation

Zsolt Fejes, Ádám Hadházi, Erzsébet Rűth, Magdolna Csávás, Ilona Bereczki, Anikó Borbás, and Pál Herczegh

Department of Pharmaceutical Chemistry, University of Debrecen, 4010 Debrecen, Hungary

E-mail: borbas.aniko@pharm.unideb.hu

Abstract: Ethyl acetoacetate-sugar derivatives were prepared by standard alkylation of primary or secondary hydroxyls of diacetonide-protected sugars with ethyl 4-chloroacetoacetate. The obtained d-fructose, d-galactose, d-glucose and d-allose derivatives were conjugated to C₆₀ using the Bingel reaction to afford hydrolytically stable, ether-linked fullerene-carbohydrates. Conjugation of an ester-protected mannose derivative to the C₆₀ scaffold was carried out by the combination of the acetoacetate chemistry with the azide-alkyne click reaction.

Keywords: fullerene – cyclopropanation – saccharides – ether linkage – click reaction

Full paper is available at www.springerlink.com.

DOI: 10.1515/chempap-2015-0087

Chemical Papers 69 (6) 896–900 (2015)