ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
Synthesis of ether-linked 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
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.
Chemical Papers 69 (6) 896–900 (2015)
Wednesday, August 10, 2022