Journal
ORGANIC LETTERS
Volume 9, Issue 22, Pages 4611-4614Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol702128z
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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.
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