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

Hiroyuki Isobe, Kaimei Cho, Niclas Solin, Daniel B. Werz, Peter H. Seeberger, Eiichi Nakamura

    Research output: Contribution to journalArticle

    87 Citations (Scopus)

    Abstract

    (Chemical Equation Presented) 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 C5-symmetry are readily produced. The cycloaddition reaction proceeds quantitatively under mild conditions without the need to protect the sugar hydroxyl groups.

    Original languageEnglish
    Pages (from-to)4611-4614
    Number of pages4
    JournalOrganic letters
    Volume9
    Issue number22
    DOIs
    Publication statusPublished - 2007 Oct 25

    ASJC Scopus subject areas

    • Biochemistry
    • Physical and Theoretical Chemistry
    • Organic Chemistry

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  • Cite this

    Isobe, H., Cho, K., Solin, N., Werz, D. B., Seeberger, P. H., & Nakamura, E. (2007). Synthesis of fullerene glycoconjugates via a copper-catalyzed huisgen cycloaddition reaction. Organic letters, 9(22), 4611-4614. https://doi.org/10.1021/ol702128z