著者
HIROYUKI HAYAKAWA KAZUHIRO HARAGUCHI HIROMICHI TANAKA TADASHI MIYASAKA
出版者
The Pharmaceutical Society of Japan
雑誌
Chemical and Pharmaceutical Bulletin (ISSN:00092363)
巻号頁・発行日
vol.35, no.1, pp.72-79, 1987-01-25 (Released:2009-10-19)
参考文献数
16
被引用文献数
29 43

The sugar moiety of adenosine, inosine, or guanosine was protected with a tert-butyldimethylsilyl group. The C-8 lithiation of these protected nucleosides was carried out with lithium diisopropylamide in tetrahydrofuran at below -70°C. The reactions of the C-8-lithiated species with MeI, HCO2Me, and ClCO2Me were examined. The resulting products having a carbon substituent at the C-8 position were converted to the corresponding 8-carbon-substituted purine nucleosides by treatment with tetrabutylammonium fluoride. The whole sequence constitutes a simple method for the preparation of 8-carbon-substituted purine nucleosides from intact purine nucleosides.