Synthesis and Properties of 2,6-Diamino-8,2'-anhydro-8-mercapto-9-β-D-arabinofuranosylpurine
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概要
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2,6-Diamino-9-β-D-ribofuranosylpurine (I) was brominated with saturated bromine-water to the 8-bromo compound (II), which was tosylated at the 2'-hydroxygroup via the 2', 3'-O-dibutylstannylene compound (III). The resulting 2,6-diamino-8-bromo-9-(2'-O-tosyl-β-D-ribofuranosyl)-purine (IV) was cyclized with thiourea in n-propanol or 40% sodium hydrogen sulfide to give 2,6-diamino-8,2'-anhydro-8-mercapto-9-β-D-arabinofuranosylpurine (V) in yields of 40% and 80%, respectively. Alternatively, 8,2'-anhydro-8-mercapto-9-β-D-arabinofuranosylguanine (VI) was acetylated and chlorinated with phosphoryl chloride to give the 2-amino-6-chloropurine-8,2'-S-cyclonucleoside derivative (VIII), which was aminated with ammonia in methanol to afford the 2,6-diaminopurine cyclonucleoside (V) in a yield of 45%. Catalytic desulfurization of the cyclonucleoside (V) gave 2,6-diamino-9-(2'-deoxy-β-D-ribofuranosyl)-purine (IX). Some physical properties of these compounds were elucidated by ultraviolet (UV), nuclear magnetic resonance (NMR) and circular dichroism (CD) spectroscopy. The CD spectra of these nucleosides and cyclonucleoside were similar to those of the corresponding adenine nucleosides and cyclonucleoside in general.
- 公益社団法人日本薬学会の論文
- 1981-12-25
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