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Communication | Special issue | Vol 42, No. 2, 1996, pp.485-488
Published online, 1st January, 1970
DOI: 10.3987/COM-95-S71
A Mild and Rapid Glycosylation Reaction between Pyrimidine Bases and 2-Deoxyribofuranosyl N,N,N',N'-Tetramethylphosphoroamidates

Takamasa Iimori, Hiroshi Kobayashi, Shun-ichi Hashimoto, and Shiro Ikegami*

*Faculty of Pharmaceutical Sciences, Teikyo University, 1091-1 Suarashi, Sagamiko-machi, Tsukui-gun, Kanagawa 199-0195, Japan

Abstract

A trimethylsilyl triflate-mediated coupling reaction to produce protected 2’-deoxynucleosides has been developed by using N,N,N’,N’-tetramethylphosphoroamidate as a leaving group. In this reaction, employment of a 3,4,5-trimethoxybenzoyl group as the 3-hydroxyl protective group in the sugar moiety improved the β-stereoselectivity via a novel 1,3-participation.