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Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors

Author

Listed:
  • Jing Zhang

    (Peking University)

  • Zhao-Xiang Luo

    (Peking University)

  • Xia Wu

    (Peking University)

  • Chen-Fei Gao

    (Peking University)

  • Peng-Yu Wang

    (Peking University)

  • Jin-Ze Chai

    (Peking University)

  • Miao Liu

    (Peking University)

  • Xin-Shan Ye

    (Peking University)

  • De-Cai Xiong

    (Peking University
    Peking University)

Abstract

Photochemical glycosylation has attracted considerable attention in carbohydrate chemistry. However, to the best of our knowledge, visible-light-promoted glycosylation via photoactive glycosyl donor has not been reported. In the study, we report a photosensitizer-free visible-light-mediated glycosylation approach using a photoactive 2-glycosyloxy tropone as the donor. This glycosylation reaction proceeds at ambient temperature to give a wide range of O-glycosides or oligosaccharides with yields up to 99%. This method is further applied in the stereoselective preparation of various functional glycosyl phosphates/phosphosaccharides, the construction of N-glycosides/nucleosides, and the late-stage glycosylation of natural products or pharmaceuticals on gram scales, and the iterative synthesis of hexasaccharide. The protocol features uncomplicated conditions, operational simplicity, wide substrate scope (58 examples), excellent compatibility with functional groups, scalability of products (7 examples), and high yields. It provides an efficient glycosylation method for accessing O/N-glycosides and glycans.

Suggested Citation

  • Jing Zhang & Zhao-Xiang Luo & Xia Wu & Chen-Fei Gao & Peng-Yu Wang & Jin-Ze Chai & Miao Liu & Xin-Shan Ye & De-Cai Xiong, 2023. "Photosensitizer-free visible-light-promoted glycosylation enabled by 2-glycosyloxy tropone donors," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-43786-y
    DOI: 10.1038/s41467-023-43786-y
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    References listed on IDEAS

    as
    1. Qian Zhu & Zhengnan Shen & Fabrizio Chiodo & Simone Nicolardi & Antonio Molinaro & Alba Silipo & Biao Yu, 2020. "Chemical synthesis of glycans up to a 128-mer relevant to the O-antigen of Bacteroides vulgatus," Nature Communications, Nature, vol. 11(1), pages 1-7, December.
    2. Mattia Silvi & Paolo Melchiorre, 2018. "Enhancing the potential of enantioselective organocatalysis with light," Nature, Nature, vol. 554(7690), pages 41-49, February.
    3. Yong Wu & De-Cai Xiong & Si-Cong Chen & Yong-Shi Wang & Xin-Shan Ye, 2017. "Total synthesis of mycobacterial arabinogalactan containing 92 monosaccharide units," Nature Communications, Nature, vol. 8(1), pages 1-7, April.
    4. Penghua Li & Haiqing He & Yunqin Zhang & Rui Yang & Lili Xu & Zixi Chen & Yingying Huang & Limei Bao & Guozhi Xiao, 2020. "Glycosyl ortho-(1-phenylvinyl)benzoates versatile glycosyl donors for highly efficient synthesis of both O-glycosides and nucleosides," Nature Communications, Nature, vol. 11(1), pages 1-10, December.
    5. Xiaojuan Zhang & Yutong Yang & Jiahao Ding & Yun Zhao & Hongbin Zhang & Yugen Zhu, 2022. "Stereoselective gold(I)-catalyzed approach to the synthesis of complex α-glycosyl phosphosaccharides," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
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