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

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

研究论文

叔丁醇锂催化N-苄基-N-叔丁氧羰基酰胺与糖的酯化反应

  • 叶丹锋 ,
  • 徐冰 ,
  • 万云辉
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  • a 宁波工程学院材料与化学工程学院 浙江宁波 315211
    b 上海中医药大学中药学院 上海 201203

收稿日期: 2024-01-30

  修回日期: 2024-04-07

  网络出版日期: 2024-04-30

基金资助

宁波工程学院启动基金(2130011540027)

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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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摘要

基于N—C键基态不稳定的策略, 报道了一种通过活化酰胺与糖类化合物发生酯化反应合成糖缀合物的新方法. 该方法采用温和的反应条件, 获得了优异的产率, 并具有广泛的底物兼容性, 展示了在糖缀合物合成中的巨大潜力. 此外, 该方法为解决糖类化合物中大空间位阻的次级羟基酯化这一具有挑战性的问题提供了一种替代途径, 并对糖类药物的发展具有促进作用.

关键词： 叔丁醇锂; N-benzyl-N-Boc酰胺; 酯化; 糖缀合物

本文引用格式

叶丹锋 , 徐冰 , 万云辉 . 叔丁醇锂催化N-苄基-N-叔丁氧羰基酰胺与糖的酯化反应[J]. 有机化学, 2024 , 44(9) : 2924 -2932 . DOI: 10.6023/cjoc202401037

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

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(叶丹锋, 陈浩, 刘志园, 雷川虎, 有机化学, 2021, 41, 1658.)
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