A concise, efficient synthesis of sugar-based benzothiazoles through chemoselective intramolecular C-S coupling
Chemical Science, ISSN: 2041-6539, Vol: 3, Issue: 7, Page: 2388-2393
2012
- 70Citations
- 19Captures
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Article Description
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. © The Royal Society of Chemistry 2012.
Bibliographic Details
Royal Society of Chemistry (RSC)
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