Novel glycosidation of 4-demethoxyanthracyclinones by the use of trimethylsilyl triflate. Syntheses of optically active 4-demethoxydaunorubicin and 4-demethoxyadriamycin.
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概要
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Optically pure (+)-4-demethoxydaunorubicin has been prepared by a novel glycosidation reaction of (+)-4-demethoxydaunomycinone with (−)-3-<I>N</I>-trifluoroacetyl-1,4-bis(<I>O</I>-<I>p</I>-nitrobenzoyl)-L-daunosamine in the presence of trimethylsilyl triflate, followed by sequential <I>O</I>- and <I>N</I>-deprotection reactions. Total synthesis of optically pure (+)-4-demethoxyadriamycin has been also accomplished by two different synthetic schemes, starting from (+)-4-demethoxydaunorubicin or by way of (+)-3′-<I>N</I>-trifluoroacetyl-4-demethoxyadriamycin. (+)-4-Demethoxyadriamycin prepared by our hands was fully characterized by its spectral properties.
- 公益社団法人 日本化学会の論文
著者
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Terashima Shiro
Sagami Chemical Res. Inst.
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SUZUKI MICHIYO
Sagami Chemical Research Center
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MATSUMOTO TERUYO
Sagami Chemical Research Center
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KIMURA YOSHIKAZU
Sagami Chemical Research Center
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Abe Rumiko
Sagami Chemical Research Center
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