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Synthesis 2020; 52(09): 1435-1443
DOI: 10.1055/s-0039-1690808
paper
© Georg Thieme Verlag Stuttgart · New York

Facile Synthesis of Novel Benzoylthiophene C-Nucleoside Analogues via Coupling of Sugar Alkynes, Aroyl Chlorides, and 1,4-Dithiane-2,5-diol

Yang Luo
a   College of Chemistry, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China   Email: zhangfy@zzu.edu.cn
,
Fei Gao
a   College of Chemistry, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China   Email: zhangfy@zzu.edu.cn
,
Hong Liu∗
a   College of Chemistry, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China   Email: zhangfy@zzu.edu.cn
,
Fuyi Zhang∗
a   College of Chemistry, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China   Email: zhangfy@zzu.edu.cn
,
Yufen Zhao
a   College of Chemistry, The Key Laboratory of Chemical Biology and Organic Chemistry of Henan Province, Zhengzhou University, Zhengzhou 450001, P. R. of China   Email: zhangfy@zzu.edu.cn
b   Institute of Drug Discovery Technology, Ningbo University, Ningbo 315211, P. R. of China
› Author AffiliationsWe gratefully acknowledge the National Natural Science Foundation of China (No. 21772180, 21272219) for financial support.
Further Information

Publication History

Received: 17 December 2019

Accepted after revision: 08 January 2020

Publication Date:
30 January 2020 (online)

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Abstract

Concise synthesis of novel benzoylthiophene C-nucleoside analogues has been achieved by the reaction of various terminal sugar alkynes with substituted benzoyl chlorides and 1,4-dithiane-2,5-diol, and subsequent dilute HCl-promoted dehydration in one pot. The sugar alkynes include pyranosides, furanosides, and acyclic sugar. The benzoyl chloride has various substituents. Twenty-eight examples are given. The desired products are obtained in 70–89% yields, and the mechanism has been clarified by isolation of the intermediate.

Key words

C-nucleoside - analogue - sugar - alkyne - thiophene - heterocycle

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0039-1690808.
  • Supporting Information
 

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