Orthogonal Triple-Click Synthesis of Heteromimetic Triglycosylated Fullerenes

Well-defined heteromultivalent glycoarchitectures remain challenging synthetic targets. Herein we report a [60]fullerene hexakis-adduct platform designed to undergo three orthogonally addressable click reactions, allowing the controlled conjugation of three distinct carbohydrates within a single nanostructure. The approach combines thiol-maleimide coupling with two sequential CuAAC transformations using protected and unprotected alkyne handles and supports both stepwise functionalization and one-pot reaction sequences. NMR and DOSY experiments confirmed the integrity and homogeneity of the resulting triple-functionalized glycofullerenes.