Syntheses of 1-epikanamycin A and its 1-N-((S)-4-amino-2-hydroxybutyryl) derivative.
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概要
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The titled compounds were prepared from 3,6′-bis(<I>N</I>-benzyloxycarbonyl)-3″-<I>N</I>-(trifluoroacetyl)kanamycin A (<B>1</B>). Oxidation of <B>1</B> with hydrogen peroxide in the presence of sodium tungstate gave the 1-hydroxyimino derivative, which, after deblocking, gave 1-deamino-1-dehydro-1-hydroxyiminokanamycin A (<B>6</B>). Reduction of <B>6</B> with Raney nickel–hydrogen in aqueous ammonia gave a mixture of kanamycin A and 1-epikanamycin A (<B>9</B>), which were separated through derivation to the corresponding tetrakis-<I>N</I>-(<I>t</I>-butoxycarbonyl) derivatives, which showed different solubility in chloroform. 1-<I>N</I>-[(<I>S</I>)-4-Amino-2-hydroxybutyryl]-1-epikanamycin A was prepared from <B>9</B> by the zinc acetate–ethyl trifluoroacetate method [to give 3,6′-bis(<I>N</I>-benzyloxycarbonyl)-1-epi-3″-trifluoroacetamidokanamycin A] followed by a regiospecific 1-<I>N</I>-acylation with (<I>S</I>)-4-benzyloxycarbonylamino-2-hydroxybutyryl group and successive deblocking.
- 公益社団法人 日本化学会の論文
著者
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Takahashi Yoshiaki
Institute For Materials Chemistry And Engineering And Department Of Molecular And Material Sciences
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Tsuchiya Tsutomu
Institute of Bioorganic Chemistry
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Umezawa Sumio
Institute of Bioorganic Chemistry
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Takahashi Yoshiaki
Institute of Bioorganic Chemistry
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Umezawa Hamao
Institute of Bioorganic Chemistry
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Fukatsu Shunzo
Central Research Laboratories, Meiji Seika Kaisha, Ltd
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Fukatsu Shunzo
Central Research Laboratories, Meiji Seika Co., Ltd.
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Suzuki Yukiko
Institute of Bioorganic Chemistry
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