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I2-mediated α-selective Ferrier glycosylation approach to synthesis of O-glycosyl amino acids

Li Ren, Yang Liu, Gui-Hua Yu, Jing-Zheng Hao, and Mao-Sheng Cheng

Key Laboratory of Structure-Based Drug Design & Discovery, Ministry of Education, Shenyang Pharmaceutical University, Shenyang, 110016, China

 

E-mail: ly_99@sina.com

Abstract: I2 is an effective promoter for the synthesis of 2,3-unsaturated glycosides via Ferrier glycosylation. This reaction was used in the present work for the synthesis of O-glycosylated Fmoc amino acid building blocks. This metal-free reaction afforded the desired products with good to excellent yields with good α-selectivity.

Keywords: O-glycosides – Ferrier rearrangement – I2 – α-selectivity

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0482-x

 

Chemical Papers 68 (4) 525–530 (2014)

Monday, September 28, 2020

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