- 著者
- Hiroyuki Hayakawa Hiromichi Tanaka Naoko Itoh Masako Nakajima Tadashi Miyasaka Kentaro Yamaguchi Yoichi Iitaka
- 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.6, pp.2605-2608, 1987-06-25 (Released:2009-10-19)
- 参考文献数
- 26
- 被引用文献数
- 30 42
The reaction of organolithium, Grignard, and organoaluminum reagents with 2'- and 3'-ketouridine derivatives was examined. For the reaction of 2', 5'-bis-0- (tert-butyldimethylsilyl) -3'-ketouridine, both organolithiums and organoaluminums seem to be practically useful. But only organoaluminums gave satisfactory yields in the reaction of 3', 5'-0- (tetraisopropyldisiloxan-1, 3-diyl) -2'-ketouridine.
- 著者
- MASAHIRO SUZUKI 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.10, pp.4056-4063, 1987-10-25 (Released:2009-10-19)
- 参考文献数
- 14
- 被引用文献数
- 4 12
Several 5-carbon-substituted 1-β-D-ribofuranosylimidazole-4-carboxamides were synthesized via the direct C-5 lithiation of a protected 4-carboxamide derivative as the key reaction step. Wittig reaction of a 5-formyl derivative was also examined.
- 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.