| Autor: |
Robins, Morris J., Hansske, Fritz, Bernier, Salwa E. |
| Zdroj: |
Canadian Journal of Chemistry; December 1981, Vol. 59 Issue: 24 p3360-3364, 5p |
| Abstrakt: |
A modified trimethylsilylation of guanosine (1) followed by in situreplacement of the 6-trimethylsilyloxy group with ammonia at 150 °C gave 2,6-diamino-9-β-D-ribofuranosylpurine (2) in 92% yield. Treatment of 2with diazomethane in the presence of tin(II) chloride dihydrate gave the 2′-O-methyl (3) and 3′-O-methyl (4) ethers of 2in 98% combined yield. The ratios of 3/4could be varied from 51:47 to 34:64 by changing the amount of catalyst used. Treatment of 3and 4with adenosine deaminase resulted in clean conversion of these 2-aminoadenosine ethers to 2′-O-methylguanosine (5) and 3′-O-methylguanosine (6), respectively, in optimized yields of 40% and 54% overall from 1. The 13C nmr data for six ribonucleosides and their isomeric methyl ether derivatives have been correlated to provide a convenient method of identification. |
| Databáze: |
Supplemental Index |
| Externí odkaz: |
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