Studies of Nucleosides and Nucleotides. LXXXI. Synthesis and Characterization of 8-Methyladenosine
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概要
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8-Methyladenosine (X) was synthesized by two ways starting from 2', 3'-O-isopropylidene-2-methylthioinosine (I). The compound (I) was methylated with t-butyl hydroperoxide in acidic media in the presence of ferrous ion to give 8-methyl compound (II) in a yield of 46%. Raney nickel dethiolation of II and acetylation at 5'-OH followed by chlorination using SOCl_2/DMF gave 6-chloro-8-methylpurine derivative (V). The compound (V) was treated with liq. NH_3 and deprotected with trifluoroacetic acid to give 8-methyladenosine (X). Alternatively II was acetylated at 5'-OH, chlorinated with Vilsmeyer-Haack reagent and treated with liq. NH_3 to give 2', 3'-O-isopropylidene-2-methylthio-8-methyladenosine (IX). The compound (IX) was deacetonized and dethiolated with Raney nickel to give X. The physical properties of X was elucidated by ultraviolet, circular dichroism and nuclear magnetic resonance spectra. A syn type conformation was assigned to 8-methyladenosine.
- 公益社団法人日本薬学会の論文
- 1977-10-25
著者
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池原 森男
Faculty of Pharmaceutical Sciences, Osaka University(Present address)
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林 元吉
Faculty of Pharmaceutical Sciences, Osaka University
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福井 寿一
Faculty Pharmaceutical Sciences, Osaka University
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福井 寿一
Faculty Pharmaceutical Sciences Osaka University
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池原 森男
Faculty Of Pharmaceutical Sciences Osaka University
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林 元吉
Faculty Of Pharmaceutical Sciences Osaka University
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