Synthesis of [60]fulleropyrrolidine glycoconjugates using 1,3-dipolar cycloaddition with C-glycosyl azomethine ylides

Heating a mixture of [60]fullerene, N-methylglycine (sarcosine), and a sugar aldehyde in refluxing toluene resulted in the formation of a complex mixture of products from which the fulleropyrrolidine monocycloadduct was isolated in 14, 10, and 12% yield for formyl C-galactopyranoside, formyl C-glucopyranoside, and formyl C-mannofuranoside, respectively.