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

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

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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.

Original languageEnglish
Pages (from-to)896-900
Number of pages5
JournalChemical Papers
Volume69
Issue number6
DOIs
Publication statusPublished - Jun 1 2015

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Keywords

  • click reaction
  • cyclopropanation
  • ether linkage
  • fullerene
  • saccharides

ASJC Scopus subject areas

  • Biochemistry
  • Chemistry(all)
  • Chemical Engineering(all)
  • Industrial and Manufacturing Engineering
  • Materials Chemistry

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