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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 9: 2924 - 2932

DOI: https://doi.org/10.6023/cjoc202401037

ARTICLES

t-BuOLi Catalyzed Esterification of N-Benzyl-N-Boc-amides with Carbohydrates

  • Danfeng Ye ,
  • Bing Xu ,
  • Yunhui Wan
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  • a College of Material Science and Chemical Engineering, Ningbo University of Technology, Ningbo, Zhejiang 315211
    b School of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203
*E-mail: ;

Received date: 2024-01-30

  Revised date: 2024-04-07

  Online published: 2024-04-30

Supported by

Startup Foundation of Ningbo University of Technology(2130011540027)

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Abstract

Based on a strategy of ground-state destabilisation of the N—C bond, a general protocol for the esterification of amides with carbohydrates was reported. This protocol offers mild reaction conditions, excellent yields, and broad substrate compatibility, thereby demonstrating great potential for the synthesis of glycoconjugates. Additionally, this method provides an alternative approach for addressing the challenging task of esterifying sterically hindered secondary hydroxyl group of carbohydrates and paving the way for advancements in carbohydrate-based pharmaceuticals.

Key words： t-BuOLi; N-benzyl-N-Boc-amides; esterification; glycoconjugates

Cite this article

Danfeng Ye , Bing Xu , Yunhui Wan . t-BuOLi Catalyzed Esterification of N-Benzyl-N-Boc-amides with Carbohydrates[J]. Chinese Journal of Organic Chemistry, 2024 , 44(9) : 2924 -2932 . DOI: 10.6023/cjoc202401037

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