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

Chao Shen; Haijun Xia; Hua Yan; Xinzhi Chen; Sadananda Ranjit; Xiaoji Xie; Davin Tan; Richmond Lee; Yanmei Yang; Bengang Xing; Kuo-Wei Huang; Pengfei Zhang; Xiaogang Liu

doi:10.1039/C2SC20248D

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

Chao Shen,^ab Haijun Xia,^a Hua Yan,^a Xinzhi Chen,^b Sadananda Ranjit,^c Xiaoji Xie,^c Davin Tan,^e Richmond Lee,^e Yanmei Yang,^f Bengang Xing,^f Kuo-Wei Huang,^e Pengfei Zhang*^a and Xiaogang Liu*^cd

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* Corresponding authors

^a College of Material Chemistry and Chemical Engineering, Hangzhou Normal University, Hangzhou, P. R. China
E-mail: chxyzpf@hotmail.com

^b Department of Chemical and Biological Engineering, Zhejiang University, Hangzhou, P. R. China

^c Department of Chemistry, National University of Singapore, 3 Science Drive 3, Singapore, Singapore
E-mail: chmlx@nus.edu.sg
Fax: +65 6779 1691

^d Institute of Materials Research and Engineering, Agency for Science and Technology and Research, 3 Research Link, Singapore, Singapore

^e KAUST Catalysis Center and Division of Chemical and Life Sciences and Engineering, King Abdullah University of Science and Technology, Thuwal, Kingdom of Saudi Arabia

^f Division of Chemistry and Biological Chemistry, Nanyang Technological University, Singapore, Singapore

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.

Chemical Science

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

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

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