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

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.

Development of Photoactive Sweet-C 60 for Pancreatic Cancer Stellate Cell Therapy

“…In addition, glycoconjugated [60]fullerenes have been investigated for enhanced cancer-targeting properties [20][21][22]. This is because cancer cells have an increased demand for glucose, which is then metabolized at a higher rate in order to generate the energy that is necessary for many features of cancer cell proliferation and tumoriogenesis [23,24].…”

Lewis Acid-Catalyzed Tandem Reaction Strategy for the Synthesis of Dihydrophenalene-Fused Lactones

“…ACS grade toluene, 1,2-dichloroethane, ethanol, ethyl acetate, and cyclopentyl methyl ether were purchased from Energy Chemical and used as received. Ester substrates 2f and 2g were prepared according to the literature procedures, 42 and other esters 2 were purchased from Energy Chemical and used as received.…”