An efficient method for the synthesis of 9-β-D-2′-deoxyribofuranosyl-6-methylpurine |
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Authors: | Shuxin Li Falong Jiang Yanjin Zhao Jinhua Guo Zhiqing Wang |
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Affiliation: | (1) Institute of Radiation and Irradiation Medicine, Academy of Military Medical Science, Beijing, 100850, China;(2) Jiangxi University of Traditional Chinese Medicine, Nanchang, 330006, China |
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Abstract: | A new method for the preparation of 9-β-D-2′-deoxyribofuranosyl-6-methylpurine from inosine (1) is described. Inosine was converted to 6-chloropurinenucleoside (4) via acetylation, chlorination, and deacetylation. Compound 4 was transformed to the key intermediate 6-methylpurinenucleoside (7) via protection of the 2′,3′,5′-hydroxy groups of 4 with 3,4-dihydropyran to give compound 5, then methylation at the 6-position of 5 with dimethyl copper lithium gave compound 6; depyranylation of 6 led to the subsequent selective protection of the 3′,5′-hydroxy groups of 7 with O[Si(I-Pr)2Cl]2 followed by reaction with phenyl chlorothionoformate to give compound 9. Compound 9 was then converted to the target compound 11 via 2′-deoxidation and 3′, 5′-desilylation. The structures of these products were identified by Mass Spectrum (MS), 1H-NMR (Nuclear Magnetic Resonance) spectra and elemental analysis. Translated from Chinese Journal of Organic Chemistry, 2006, 26(10): 1394–1397 (in Chinese) |
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Keywords: | nucleoside purinenucleoside synthesis |
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