- 著者
- 上杉 晴一 三木 弘子 池原 森男
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.29, no.8, pp.2199-2204, 1981-08-25 (Released:2008-03-31)
- 参考文献数
- 41
- 被引用文献数
- 3 7
^<13>C nuclear magnetic resonance spectra of various 2'-substituted 2'-deoxyadenosines are presented. The relative substituent chemical shifts of each sugar carbon are analyzed in terms of a substituent electronegativity parameter and compared with the data for substituted cyclohexanes. The relative substituent chemical shifts of C2' and C4' are controlled mainly by the inductive effect of the substituent. Those of C1' and C3' cannot be interpreted by inductive effect only. Some effect which is perturbed by the presence of a cis-substituent seems to be operating. A good linear correlation was observed between the substituent chemical shift of C2' and the N conformer population in the furanose puckering equilibrium.
- 著者
- 池原 森男 三木 弘子
- 出版者
- The Pharmaceutical Society of Japan
- 雑誌
- Chemical and Pharmaceutical Bulletin (ISSN:00092363)
- 巻号頁・発行日
- vol.26, no.8, pp.2449-2453, 1978-08-25 (Released:2008-03-31)
- 被引用文献数
- 23 36
9-(2'-O-Methanesulfonyl- or trifluoromethanesulfonyl-3', 5'-di-O-tetrahydropyranyl-β-D-arabinofuranosyl) adenine (Ia, b) were reacted with lithium chloride or tetrabutylammonium halide to yield 2'-halogeno-2'-deoxy compounds (IIa-d). These halogeno compounds were deprotected with 80% acetic acid to give 2'-chloro-, 2'-bromo-, 2'-fluoro and 2'-iodo-2'-deoxyadenosine (IVa-d) in overall yields of 12-25% from the compound I. Ultraviolet absorption properties, 1H and 13C-nuclear magnetic resonance spectral properties were recorded on the compounds IVa-d.