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An Efficient Approach to the Synthesis of Nucleosides: Gold(I)-Catalyzed N-Glycosylation of Pyrimidines and Purines with Glycosyl ortho-Alkynyl Benzoates

Authors

  • Qingju Zhang,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
    2. Department of Chemistry, Zhengzhou University (China)
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  • Dr. Jiansong Sun,

    Corresponding author
    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
    • State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Yugen Zhu,

    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • Dr. Fuyi Zhang,

    1. Department of Chemistry, Zhengzhou University (China)
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  • Prof. Biao Yu

    Corresponding author
    1. State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
    • State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032 (China), Fax: (+86) 21-6416-6128
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  • This research was financially supported by the National Natural Science Foundation of China (20932009 and 20921091), the National Basic Research Program of China (2010CB529706), and the E-Institute of Shanghai Municipal Education Commission (E09013).

Abstract

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Überredet mit Gold: Die Titelreaktion liefert in Gegenwart von [Ph3PAuNTf2] (Tf=Trifluormethansulfonyl) bequem und hoch regioselektiv die jeweiligen Nucleoside (siehe Schema). Sogar Purinderivate können umgesetzt werden, weil die milden Bedingungen den Einsatz von Schutzgruppen ermöglichen, die mit den gängigen N-Glycosylierungsbedingungen inkompatibel sind.

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