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

doi:10.6023/cjoc202401037

Chinese Journal of Organic Chemistry Previous Articles Next Articles

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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^a,*, 徐冰^a, 万云辉^b,*

^a宁波工程学院材料与化学工程学院宁波 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
基金资助:
宁波工程学院启动基金(No. 2130011540027)资助项目.

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

Danfeng Ye^a,*, Yun-hui Wan^b

^aCollege of Material Science and Chemical Engineering, Ningbo University of Technology, Ningbo 315211;
^bSchool of Pharmacy, Shanghai University of Traditional Chinese Medicine, Shanghai 201203

Received:2024-01-30 Revised:2024-04-07
Contact: * E-mail: 13023288301@163.com
Supported by:
Ningbo University of Technology (No. 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

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Danfeng Ye, Yun-hui Wan. t-BuOLi Catalyzed Construction of Glycoconjugates by Esterification of N-Benzyl-N-Boc-amides with Carbohydrates[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202401037.

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叔丁醇锂催化N-苄基-N-叔丁氧羰基酰胺与糖的酯化反应

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

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