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Synthesis 2020; 52(09): 1435-1443
DOI: 10.1055/s-0039-1690808
DOI: 10.1055/s-0039-1690808
paper
Facile Synthesis of Novel Benzoylthiophene C-Nucleoside Analogues via Coupling of Sugar Alkynes, Aroyl Chlorides, and 1,4-Dithiane-2,5-diol
We 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)
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.
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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