Expeditious Preparation of N-Fmoc 2-Aminoethanesulfonyl Chlorides with Functionalized 1-Substituents
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Published:2018-04-24
Issue:2
Volume:15
Page:246-255
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ISSN:1570-1794
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Container-title:Current Organic Synthesis
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language:en
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Short-container-title:COS
Author:
Haiouani Kheira1,
Chen Xingpeng1,
Xu Jiaxi1
Affiliation:
1. State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, Faculty of Science, Beijing University of Chemical Technology, Beijing 100029, China
Abstract
Aim and Objective: [(9H-Fluoren-9-yl)methoxy]carbonyl (Fmoc)-protected 2-aminoethanesulfonyl
chlorides with various functionalized 1-substituents may be of use as building blocks for the Fmoc strategic
synthesis of sulfonopeptides.
Materials and Method:
Fmoc-protected 2-aminoethanesulfonyl chlorides with different functionalized 1-
substituents were synthesized via radical addition of N-Fmoc allylamine and xanthates with functionalized Ssubstituents,
and subsequent oxidative chlorination with N-chlorosuccimide/HCl.
Results:
Fmoc-protected 2-aminoethanesulfonyl chlorides with different functionalized 1-substituents were
synthesized via radical addition and subsequent oxidative chlorination. The mechanism on the oxidative chlorination
is proposed.
Conclusion:
The current method is an expeditious, convenient, and practical method for the synthesis of Fmocprotected
2-aminoethanesulfonyl chlorides with different functionalized 1-substituents in good to excellent
yields.
Publisher
Bentham Science Publishers Ltd.
Subject
Organic Chemistry,Biochemistry
Cited by
3 articles.
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1. Oxidation and Reduction;Organic Reaction Mechanisms Series;2021-08-27
2. Radical Reactions;Organic Reaction Mechanisms Series;2021-08-27
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