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

摘要

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 C-60 using the Bingel reaction to afford hydrolytically stable, ether-linked fullerene-carbohydrates. Conjugation of an ester-protected mannose derivative to the C-60 scaffold was carried out by the combination of the acetoacetate chemistry with the azide-alkyne click reaction. (C) 2015 Institute of Chemistry, Slovak Academy of Sciences