ISSN print edition: 0366-6352 ISSN electronic edition: 1336-9075 Registr. No.: MK SR 9/7 Published monthly

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)