Jump to main content
Jump to site search
Access to RSC content Close the message box

Continue to access RSC content when you are not at your institution. Follow our step-by-step guide.


Issue 7, 2012
Previous Article Next Article

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

Author affiliations

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

Back to tab navigation

Supplementary files

Article information


Submitted
28 Feb 2012
Accepted
08 May 2012
First published
08 May 2012

Chem. Sci., 2012,3, 2388-2393
Article type
Edge Article

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

Social activity

Search articles by author

Spotlight

Advertisements