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Paper | Regular issue | Vol 89, No. 1, 2014, pp.69-81
Published online, 12th December, 2013
DOI: 10.3987/COM-13-12861
Ferrier Glycosylation Reaction Catalyzed by Bi(OTf)3-Montmorillonite K-10: Efficient Synthesis of 3,4-Unsaturated Sialic Acid Derivatives: Synthesis and Biological Evaluation as Inhibitors of Human Parainfluenza Virus Type 1

Mai Oba, Yayoi Ueno, Satoru Kitani, Takuya Hayakawa, Tadanobu Takahashi, Takashi Suzuki, Masayuki Sato, and Kiyoshi Ikeda*

*Department of Pharmaceutical Sciences, Hiroshima International University, 5-1-1, Hirokoshingai, Kure, Hiroshima, 737-0112, Japan

Abstract

The reaction of the 4,5-oxazoline derivative of sialic acid with various alcohols was effectively promoted by a catalytic amount of montmorillonite K-10 clay-supported Bi(OTf)3 to produce a variety of 3,4-unsaturated sialic acids via the Ferrier glycosylation reaction in moderate yields. The deprotection of the isopropylidene group and hydrolysis of the ester group of 7a-g gave 4a-f, whose inhibitory activities against hPIV-1 sialidase were studied.