Synthesis of aryl α-O-L-rhamnopyranoside by two-step reaction in one pot

GRAPHICAL ABSTRACT

ABSTRACT

The title compounds were conveniently synthesized by a phase transfer catalyzed approach in two steps and one pot using the rhamnopyranosyl chloride as key intermediate. The two-step one-pot procedure is more convenient and environmentally friendly, compared to the published synthetic routes. Besides, the structure-reactivity relationship and the plausible mechanism for this base-catalyzed glycosylation were discussed by means of the Hammett equation.

KEYWORDS:

• Rhamnoside
• rhamnopyranosyl chloride
• phase transfer catalysis
• α-O-aryl rhamnoside

Acknowledgements

We sincerely thank the analytic center of East China Normal University for data measurements. We appreciate Ms Chunjuan Shi, Mr Wei Liu, Mr Simin Zhou, Mr Haoqiang Qi, and Mr Wenshuai Si for helpful discussion. The project was supported by “DAXIA” Science Research Foundation of East China Normal University (KY2005–017), Shanghai Pujiang Program (05PJ14315), Shanghai Rising-Star Program (06QA14018), the Natural Science Foundation of Shanghai (11ZR1410400) and large instruments Open Foundation of East China Normal University (2012–92, 20151043 &20162015).

Additional information

Notes on contributors

Nianping Liu

Nianping Liu received his B.S. in chemistry in 2006 from East China Normal University, China. He obtained his Ph.D. in 2014 from Graduate University of Chinese Academy of Sciences, China. He is currently working as a senior scientist at the Shanghai Chemspec Corporation, China.

Jianbo Zhang

Jianbo Zhang received his B.S. in pharmacy in 1993 from Fudan University, China. He obtained his M.S. in 1996 and Ph.D. in 1999 from the Shanghai Institute of Organic Chemistry. In 2000, he joined Wayne State University as a postdoctoral position to study recombinant glycoenzymes for synthetic applications. He joined the faculty at East China Normal University in 2003, where he is now an associate professor at the School of Chemistry and Molecular Engineering. His research interests are syntheses of glycoconjugates and green heterogeneous catalysts for carbohydrate chemistry.