Synthesis of Cyclic α-Amino Acids. IV. Syntheses of Adenine Nucleosides of 3-Amino-3-<I>C</I>-carboxy-3-deoxy-D-ribofuranose and 3-Amino-3-<I>C</I>-carboxy-3-deoxy-D-ribopyranose
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概要
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9-(3′-Amino-3′-<I>C</I>-carboxy-3′-deoxy-β-D-ribofuranosyl)adenine (I) and 9-(3′-amino-3′-<I>C</I>-carboxy-3′-deoxy-β-D-ribopyranosyl)adenine (II) have been synthesized. They are the first examples of nucleoside-derivatives which have an α-amino acid structure in their furanose or pyranose ring. A masked derivative (VII) of α-D-<I>erythro</I>-pentofuranos-3-ulose was converted into a hydantoin derivative (IX), which was acetolyzed and then treated with dry hydrogen chloride to give an acylglycosyl chloride (XI). Condensation of this derivative with chloromercuri-6-benzamidopurine followed by hydrolysis afforded I. Treatment of the hydantoin derivative (IX) with methanolic hydrogen chloride followed by hydrolysis gave methyl 3-amino-3-<I>C</I>-carboxy-3-deoxy-α-D-ribopyranoside (XVII), which has been found to be identical with one of the isomers of methyl 3-amino-3-<I>C</I>-carboxy-3-deoxy-α-D-pentopyranoside previously reported. The 1-<I>O</I>-acetyl-3-<I>N</I>-benzoyl-2,4-di-<I>O</I>-benzoyl derivative of ethyl ester of this acid (XVII) was fused with 6-benzamidopurine in the presence of <I>p</I>-toluenesulfonic acid and followed by hydrolysis to afford II. Structural proofs for the new nucleoside-derivatives were obtained from their ultraviolet, infrared and nuclear magnetic resonance spectra.
- 公益社団法人 日本化学会の論文
著者
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Nakada Saburo
Department of Applied Chemistry Faculty of Engineering Keio Univerity
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Kinoshita Mitsuhiro
Department of Applied Chemistry Engineering Faculty of Keio University
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Umezawa Sumio
Department of Applied Chemistry Engineering Faculty Keio University
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Yanagisawa Hiroaki
Department of Applied Chemistry, Faculty of Engineering, Keio University
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Nakada Saburo
Department of Applied Chemistry, Faculty of Engineering, Keio University
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