Synthesis of fullerene glycoconjugates via a copper-catalyzed Huisgen cycloaddition reaction

The synthesis of fullerene-carbohydrate conjugates using a copper-catalyzed [3 + 2] cycloaddition reaction to facilitate the union of an azido-functionalized sugar and a pentaalkynyl[60]fullerene is straightforward, Thus, fullerenes bearing five oligosaccharides such as Gb3-trisaccharide can be readily accessed. Nanometer-scale molecular architectures presenting as many as 15 sugar moieties in C-5-symmetry are readily produced. The cycloaddition reaction proceeds quantitatively under mild conditions without the need to protect the sugar hydroxyl groups.