Studies on Aminosugars. XXIX. Syntheses of Nucleosides of 3-Amino-3-deoxy-3-<I>C</I>-hydroxymethyl-β-D-ribofuranose
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概要
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Reduction of 3-acetamido-3-<I>C</I>-carboxy-3-deoxy-1,2-<I>O</I>-isopropylidene-α-D-ribofuranose-y-lactone (<B>1</B>) with lithium aluminum hydride or sodium borohydride followed by acetylation gave 3-acetamido-3-<I>C</I>-acetoxymethyl-5-<I>O</I>-acetyl-3-deoxy-1,2-<I>O</I>-isopropylidene-α-D-ribofuranose (<B>2</B>). Hyrdolysis of <B>2</B> followed by <I>N</I>-phthaloylation and <I>O</I>-acetylation gave 3-<I>C</I>-acetoxymethyl-5-<I>O</I>-acetyl-3-deoxy-1,2-<I>O</I>-isopropylidene-3-phthalimido-α-D-ribo-furanose (<B>7</B>), which was acetolyzed and chlorinated to give acylglycosyl chloride (<B>9</B>). Condensation of <B>9</B> with 6-benzamidopurine followed by aminolysis afforded 9-(3′-amino-3′-deoxy-3′-<I>C</I>-hydroxymethyl-β-D-ribofuranosyl) adenine (<B>11</B>). 6-dimethylaminopurine, guanine, cytosine and uracil derivatives were similarly synthesized.
- 公益社団法人 日本化学会の論文
著者
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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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