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Paper | Regular issue | Vol 32, No. 12, 1991, pp.2451-2470
Published online, 1st January, 1970
DOI: 10.3987/COM-91-5884
Synthesis of 2’,3’-Didehydro-2’,3’-dideoxynucleosides Utilizing Coupling Reactions between Nucleic Bases and Phenylthio-substituted 2,3-Dideoxyribose

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

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


Stereoselectivities in coupling reactions between silylated pyrimidine bases and 3- or 2-α-phenylthio-2,3-dideoxyribose were examined. In the former case, no stereoselectivities were observed when the coupling reactions were performed either with 1-chlorosugar in an SN2 mode or in the presence of Lewis acids as catalyst in an SN1 mode. Coupling reaction with 2-α-phenylthio-2,3-dideoxyribose in the presence of Lewis acids, especially SnCl4, proceeded with good stereoselectivity to give anomeric mixtures of α:β = 1:9. All these nucleosides were converted to 2’,3’-didehydro-,2’,3’-dideoxynucleosides by oxidation to sulfoxides followed by thermal elimination of sulfenic acid.