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A new synthesis of 5'-deoxy-8,5'-cyclo-adenosine and -inosine: conformationally-fixed purine nucleosides (nucleosides and nucleotides. XVI).

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Title: A new synthesis of 5'-deoxy-8,5'-cyclo-adenosine and -inosine: conformationally-fixed purine nucleosides (nucleosides and nucleotides. XVI).
Authors: Matsuda, Akira Browse this author
Muneyama, Kei Browse this author
Nishida, Takako Browse this author
Sato, Tatsuo Browse this author
Ueda, Tohru Browse this author
Issue Date: Dec-1976
Publisher: Oxford University Press
Journal Title: Nucleic acids research
Volume: 3
Issue: 12
Start Page: 3349
End Page: 3357
Publisher DOI: 10.1093/nar/3.12.3349
PMID: 01005121
Abstract: A versatile method for the synthesis of 5'-deoxy-8,5'-cycloadenosine, a conformationally-fixed "anti" type of adenosine, was presented. Irradiation of 2', 3'-O-isopropylidene-5'-deoxy-5'-phenylthioadenosine with 60W Hg vapor lamp afforded 2',3'-O-isopropylidene-5'-deoxy-8,5'-cycloadenosine in high yield. The use of other 5'-alkylthio derivatives also gave the cycloadenosine, though the yields were rather poor. Deacetonation of the cyclocompound with 0.1N HCl gave 5'-deoxy-8,5'-cycloadenosine. The cycloinosine derivative was similarly prepared. The nmr, mass and CD spectra of 5'-deoxy-8,5'-cycloadenosine were given and discussed with the previously reported results.
Type: article
URI: http://hdl.handle.net/2115/46973
Appears in Collections:薬学研究院 (Faculty of Pharmaceutical Sciences) > 雑誌発表論文等 (Peer-reviewed Journal Articles, etc)

Submitter: 松田 彰

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