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Paper | Regular issue | Vol 31, No. 11, 1990, pp.2041-2054
Published online, 1st January, 1970
DOI: 10.3987/COM-90-5563
Stereoselectivities in the Coupling Reaction between Silylated Pyrimidine Bases and 1-Halo-2,3-dideoxyribose

Hiroshi Kawakami,* Takashi Ebata, Koshi Koseki, Katsuya Matsumoto, Hajime Matsushita, Yoshitake Naoi, and Kazuo Itoh

*Life Science Research Laboratory, Japan Tobacco Inc., 6-2, Umegaoka, Midori-ku, Yokohama, Kanagawa 227-8512, Japan

Abstract

Coupling reactions between 1-chloro-2,3-dideoxyribose and silylated pyrimidines between have been examined from the point of stereoselectively. When the reaction was carried out in chloroform, the selectively was in the anomeric ratio of α:β-4:6. On the other hand, the presence of tertiary amine raises the selectively to α:β-7:3,