Studies of Nucleosides and Nucleotides. LXXIX. Purine Cyclonucleosides. (37). The Total Synthesis of an Antibiotic 2'-Amino-2'-deoxyguanosine
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概要
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An antibiotic 2'-amino-2'-deoxyguanosine (I) was synthesized chemically from a guanine 8,2'-O-cyclonucleoside (II), which could be obtained from guanosine. Compound (II) was converted to N^2,3', 5'-triacetyl derivative (III), which was subjected to opening of the anhydro linkage with liq. H_2S in pyridine. Resulting 8-mercaptoarabinofuranosylguanine (IV) was dethiolated and mesylated to give N^2,3', 5'-triacetyl-2'-mesylarabinosylguanine (VI). Deprotection of VI and reprotection with tetrahydropyranyl groups gave compound VIII. Reaction of the compound VIII with sodium azide in acetamide at 210°for 10 min gave 2'-azido compound (IX). The compound IX was deprotected to give 2'-azido-2'-deoxyguanosine (X). Raney nickel catallyzed hydrogenolysis of X gave 2'-amino-2'-deoxyguanosine, which was proved to be identical with a sample of the antibiotic.
- 公益社団法人日本薬学会の論文
- 1978-01-25
著者
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丸山 徳見
Faculty of Pharmaceutical Sciences, Tokushima Bunri University
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丸山 徳見
Department Of Pharmaceutical Sciences Tokushima Bunri University
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池原 森男
Faculty Of Pharmaceutical Sciences Osaka University
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丸山 徳見
Faculty of Pharmaceutical Sciences, Osaka University
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