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Paper | Regular issue | Vol 34, No. 11, 1992, pp.2117-2121
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6125
Facile Stereospecific Synthesis of α-Anomeric 2’-Deoxynucleosides

Kazuo Shinozuka,* Yoshiki Hirota, Tsutomu Morita, and Hiroaki Sawai

*Department of Chemistry, Faculty of Engineering, Gunma University, Tenjincho, Kiryu City 376, Japan

Abstract

The coupling reaction of activated nucleobases, such as the sodium salts of N-benzoyladenine and 6-chloropurine and 2,4-bis-O-trimethylsilylthymine, with 1-α-chloro-2-deoxy-3,5-di-O-p-toluoylribofuranose (1) in a mixture of acetonitrile and tetrahydrofuran leads to the stereospecific formation of α-anomeric 2’-deoxynucleosides with satisfactory yields. The ratio of the distribution between the resulted α- and β-stereoisomers was about 3:1 in each case. The method is simple and applicable to the preparation of both purine and pyrimidine α-2’-deoxynucleosides.