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Issue 7, 2012
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A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C–S coupling

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Abstract

Sugar-based benzothiazoles are a new class of molecules promising for many biological applications. Here, we have synthesized a wide range of sugar-based benzothiazoles from readily accessible glycosyl thioureas by chemoselective, palladium-catalyzed C–S coupling reactions. Corroborated by theoretical calculations, a mechanistic investigation indicates that the coordination to the palladium by a pivaloyl carbonyl group and the presence of intramolecular hydrogen bonding play important roles in the efficiency and chemoselectivity of reaction. These fluorescent glycoconjugates can be observed to readily enter mammalian tumor cells and exhibit potential in vitro antitumor activity.

Graphical abstract: A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C–S coupling

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Publication details

The article was received on 28 Feb 2012, accepted on 08 May 2012 and first published on 08 May 2012


Article type: Edge Article
DOI: 10.1039/C2SC20248D
Citation: Chem. Sci., 2012,3, 2388-2393
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    A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C–S coupling

    C. Shen, H. Xia, H. Yan, X. Chen, S. Ranjit, X. Xie, D. Tan, R. Lee, Y. Yang, B. Xing, K. Huang, P. Zhang and X. Liu, Chem. Sci., 2012, 3, 2388
    DOI: 10.1039/C2SC20248D

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