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

  • Zsolt Fejes , Ádám Hadházi , Erzsébet Rűth , Magdolna Csávás , Ilona Bereczki , Anikó Borbás EMAIL logo and Pál Herczegh
Published/Copyright: March 19, 2015
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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.

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Received: 2014-9-28
Revised: 2014-11-23
Accepted: 2014-11-27
Published Online: 2015-3-19
Published in Print: 2015-6-1

© 2015 Institute of Chemistry, Slovak Academy of Sciences

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