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A new and improved process for C-aryl glucoside SGLT2 inhibitors

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Abstract

A practical and scalable synthesis of C-glycosides identified as highly potent sodium-dependent glucose transporter 2 (SGLT2) inhibitors is described. Highlights of the synthetic process are a concise, ten-step synthesis of a structurally complex active pharmaceutical ingredient from a known intermediate via a selective and quantitative addition of an aryl species to the Weinreb amide, and the isomers of undesired ortho-products were avoided during the preparation. The chemistry developed has been applied to prepare SGLT2 inhibitors without recourse to chromatography.

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Acknowledgements

This work was financially supported by Jiangsu Province Natural Science Fund (20131414) and by the National Natural Science Foundation of China (51403104).

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Authors and Affiliations

  1. School of Pharmacy, Nanjing University of Chinese Medicine, Nanjing, 210046, China

    Yonghai Liu & Chunyan Ou

  2. Jiangsu Collaborative Innovation Center of Chinese Medicinal Resources Industrialization, Nanjing, 210046, China

    Tingming Fu

  3. Shanghai Oasis Fine Chemicals Co., Ltd., Shanghai, 200127, China

    Zhidong Chen

Authors
  1. Yonghai Liu
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  2. Tingming Fu
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  3. Zhidong Chen
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  4. Chunyan Ou
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Correspondence to Yonghai Liu.

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Liu, Y., Fu, T., Chen, Z. et al. A new and improved process for C-aryl glucoside SGLT2 inhibitors. Monatsh Chem 146, 1715–1721 (2015). https://doi.org/10.1007/s00706-015-1458-z

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  • DOI: https://doi.org/10.1007/s00706-015-1458-z

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