Reaction of 6-Methylsulfonylpurine Riboside with Carbon Nucleophiles and the Synthesis of 6-Alkylpurine Nucleosides (Nucleosides and Nucleotides. XXIX)
Yamane, A; Matsuda, A; Ueda, T
| HERO ID | 4933090 |
|---|---|
| In Press | No |
| Year | 1980 |
| Title | Reaction of 6-Methylsulfonylpurine Riboside with Carbon Nucleophiles and the Synthesis of 6-Alkylpurine Nucleosides (Nucleosides and Nucleotides. XXIX) |
| Authors | Yamane, A; Matsuda, A; Ueda, T |
| Journal | Chemical and Pharmaceutical Bulletin |
| Volume | 28 |
| Issue | 1 (1980) |
| Page Numbers | 150 |
| Abstract | Treatment of 6-methylsulfonyl-9-(2, 3, 5-tri-O-benzoyl-β-D-ribofuranosyl) purine with ethyl acetoacetate and sodium hydride in tetrahydrofuran afforded, after deblocking, 6-ethoxycarbonylmethyl-9-β-D-ribofuranosylpurine. Similarly, replacement of the 6-methylsulfonyl moiety with other carbanions derived from diethyl malonate, ethyl cyanoacetate, malononitrile, nitromethane, and sodium cyanide gave the corresponding 6-C-substituted purine nucleosides. Most of these derivatives exist as the 6-(1H)-exomethylene tautomeric forms. 6-Ethoxycarbonylmethylpurine riboside was further converted to 6-methyl, ethyl, propyl, butyl, and pentyl-purine ribosides by decarboxylation or prior alkylation of the methylene group followed by de-carboxylation. This reaction sequence facilitated the preparation of hitherto almost inaccessible alkyl or C-substituted purine nucleosides. |
| Is Certified Translation | No |
| Dupe Override | No |
| Is Public | Yes |