Online article for Non-subscribers

Pay per view

Heterocycles has a pay-per-view service for Non-subscribers.
You will be able to directly purchase the full text article through PayPal.
Your purchased Paper can be downloaded after the payment is completed.
An e-mail will be sent the URL to download the paper.
If you have any questions, please contact: purchase@heterocycles.com

Price: ¥ 4,320 (Yen only)
Period: This Article can be accessed for 7 days.

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

Abstract

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.