ISSN print edition: 0366-6352
ISSN electronic edition: 1336-9075
Registr. No.: MK SR 9/7
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
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.
Chemical Papers 68 (4) 525–530 (2014)