著者

松田 彰 渡辺 一之 宮坂 貞 上田 亨

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.37, no.2, pp.298-303, 1989-02-25 (Released:2008-03-31)

参考文献数

16

被引用文献数

3 5

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The synthesis of a new carbon-bridged cyclopurine nucleoside, 2'-deoxy-8, 2'-methanoguanosine (25), which is fixed in a high-anti torsional angle region, was accomplished. 2-Acetamido-6-ethoxy-8-methanesulfonyl-9-(3, 5-di-O-acetyl-2-O-tosyl-1-β-D-ribofuranosyl)purine (18) was cyclized with carbanions of malonic esters, followed by sequential deblocking and decarboxylation to afford 25. The ultraviolet spectra of 25 in neutral solution revealed two separated bands corresponding to their B1u and B2u transitions, which was rather similar to the case of its O6-ethyl derivative (22), but quite different from the previously reported 8, 2'-methanoguanosine (26), a ribosyl counterpart of 25. The circular dichroism spectra of these cyclonucleosides are also discussed.