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Concise synthesis of thiophene C-nucleoside analogues bearing sugar residue and aromatic residue through dimerization and sulfur heterocyclization of sugar alkynes and substituted iodoethynylbenzene

Abstract

The synthesis of thiophene C-nucleoside analogues bearing sugar residue (mono- and disaccharides) and aromatic residue has been achieved by symmetric dimerization of terminal sugar alkynes or unsymmetric dimerization of terminal sugar alkynes and substituted iodoethynylbenzene followed by sulfur heterocyclization in one pot. Homocoupling of terminal sugar alkyne and subsequent sulfur heterocyclization produce thiophene C-nucleoside analogues bearing disaccharides. Unsymmetric dimerization of terminal sugar alkyne and substituted iodoethynylbenzene followed by sulfur heterocyclization give those bearing monosaccharide and aromatic residue. This approach is concise, general and mild, which is suitable for structurally diversified pyranosides, furanosides, and acyclic sugars. Thirty-two examples have been given and the corresponding products are obtained in moderate to excellent yields.

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Article information


Submitted
21 Dec 2019
Accepted
12 Feb 2020
First published
13 Feb 2020

Org. Biomol. Chem., 2020, Accepted Manuscript
Article type
Paper

Concise synthesis of thiophene C-nucleoside analogues bearing sugar residue and aromatic residue through dimerization and sulfur heterocyclization of sugar alkynes and substituted iodoethynylbenzene

X. Zhou, T. Jia, Y. Luo, H. Liu, F. Zhang and Y. Zhao, Org. Biomol. Chem., 2020, Accepted Manuscript , DOI: 10.1039/C9OB02717C

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