著者

吉村 祐一 / 上田 享 松田 彰 Akira MATSUDA

出版者

The Pharmaceutical Society of Japan

雑誌

Chemical and Pharmaceutical Bulletin (ISSN:00092363)

巻号頁・発行日

vol.40, no.7, pp.1761-1769, 1992-07-25 (Released:2008-03-31)

参考文献数

49

被引用文献数

20 28

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6, 1'-Propanouridine (10), a carbon-bridged cyclouridine fixed in the syn-conformation, was synthesized from D-fructose. Two additional carbon-units were introduced at the 1'-position of 1'-hydroxymethyl-O2, 2'-anhydrouridine 13 and inversion of the 2' hydroxyl group was achieved by sequential oxidation-reduction reactions. Finally, the spiro-carbon bridge was constructed by radical cyclization of the 1'-iodopropyl derivative of 5-chlorouridine. Dehydrochlorination followed by deprotection gave the desired 10. The circular dichroism (CD) spectrum of 10 showed a negative Cotton effect ([θ]=-6100) at the main absorption region, whereas 5'-O-tert-butyldimethylsilyl-2', 3'-O-isopropylidene-6, 1'-propanouridine (30) showed almost no Cotton band at the same absorption region. These results suggest that the critical region in which the CD Cotton effect changes from negative to positive is present in the syn region where 10 is located. Correlation of the magnitude and the direction of the sign of the CD Cotton effect and the torsion angle (χ) is also discussed.

著者

吉村 祐一

出版者

北海道大学

巻号頁・発行日

1991

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Hokkaido University(北海道大学). 博士(薬学)

著者

吉村 祐一

出版者

東北薬科大学

雑誌

東北薬科大学研究誌 (ISSN:1345157X)

巻号頁・発行日

vol.61, pp.1-10, 2014-12

著者

吉村 祐一

出版者

東北薬科大学

雑誌

東北薬科大学研究誌 (ISSN:1345157X)

巻号頁・発行日

vol.55, pp.9-22, 2008-12