Stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis

Science China Chemistry (2021)Cite this article

Abstract

Herein, we reported the stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis and found a suitable system to resolve many challenges, such as the tolerance towards the density of functional groups, the variability of the anomeric position, the compatibility of appropriate catalyst combinations, the regioselectivity of nucleophiles, and the match/mismatch problems between chiral substrates and chiral ligand-metal complexes. The method enables the efficient preparation of a series of unnatural C-glycosamino acid skeletons bearing two contiguous stereogenic centers in good yields with excellent diastereos-electivity. From this crucial precursor, various C-glycosamino acid derivatives have been achieved diversely. The readily prepared C-glycosamino acid hybrids will meet the growing demands for the development of new molecular entities for discovering new drugs and materials. This stereodivergent synthesis of C-glycosamino acids will further accelerate the study of their structural features, mode of action, and potential biological applications in the near future.

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Acknowledgements

This work was supported by the National Natural Science Foundation of China (051170001, 21772084, 22071087), the Fundamental Research Funds for the Central Universities (lzujbky-2017-k06) and the Open Projects Funds of Shandong Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University (2019CCG05). Xiaolei Wang thanks the Thousand Young Talents Program for financial support. We also thank Sumit O. Bajaj (Corden Pharma Boulder) for language polishing and Prof. Quanxiang Wu & Ya Li for giving suggestion towards the absolute configuration determining via CD spectra.

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Author notes

  1. These authors contributed equally to this work.

Affiliations

  1. State Key Laboratory of Applied Organic Chemistry, Department of Chemistry and School of Pharmacy, Lanzhou University, Lanzhou, 730000, China

    Xiaoxiao Yan, Feng Feng, Lin Zhou, Linrong Chen, Shouchu Tang, Jian Liu & Xiaolei Wang

  2. The National Glycoengineering Research Center and Shandong Provincial Key Laboratory of Carbohydrate Chemistry and Glycobiology, Shandong University, Qingdao, 266237, China

    Feng Cai

Authors
  1. Xiaoxiao Yan
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  2. Feng Feng
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  3. Lin Zhou
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  4. Linrong Chen
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  6. Jian Liu
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  7. Feng Cai
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Correspondence to Jian Liu or Xiaolei Wang.

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The supporting information is available online at http://chem.scichina.com and http://link.springer.com/journal/11426. The supporting materials are published as submitted, without typesetting or editing. The responsibility for scientific accuracy and content remains entirely with the authors.

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Yan, X., Feng, F., Zhou, L. et al. Stereodivergent synthesis of C-glycosamino acids via Pd/Cu dual catalysis. Sci. China Chem. (2021). https://doi.org/10.1007/s11426-020-9930-7

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Keywords

  • C-glycosamino acid
  • glycomimetics
  • peptidomimetics
  • stereodivergent
  • dual catalysis