Syntheses of 23-C-substituted derivatives of mycaminosyl tylonolide and 4'-deoxymycaminosyl tylonolide.
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概要
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23-C-Substituted derivatives of mycaminosyl tylonolide (MT) and 4′-deoxymycaminosyl tylonolide (DT) have been prepared by the reaction of protected 23-aldehyde derivatives, 2′,4′-di-<I>O</I>-acetyl-3-<I>O</I>-<I>t</I>-butyldimethylsilyl-23-deoxy-23-oxomycaminosyl tylonolide diethyl acetal (<B>5</B>) and 2′-<I>O</I>-acetyl-3-<I>O</I>-<I>t</I>-butyldimethylsilyl-23,4′-dideoxy-23-oxomycaminosyl tylonolide diethyl acetal (<B>26</B>), with several Grignard reagents and methyllithium. The final products were (23<I>S</I>)- and (23<I>R</I>)-23-C-methyl (<B>13a</B>, <B>13b</B>), -ethyl (<B>14a</B>, <B>14b</B>), -butyl (<B>15a</B>, <B>15b</B>), -phenyl (<B>16b</B>, <B>16a</B>), -allyl (<B>17a</B>, <B>17b</B>), -vinyl (<B>18a</B>, <B>18b</B>), -ethynyl (<B>19b</B>, <B>19a</B>) derivatives of MT, and (23<I>S</I>)- and (23<I>R</I>)-23-C-methyl (<B>28a</B>, <B>28b</B>), -vinyl (<B>29a</B>, <B>29b</B>), and -ethynyl (<B>30b</B>, <B>30a</B>) derivatives of DT. Their configurations at 23-position were determined by the NOE difference spectroscopy on <B>13a</B> and <B>13b</B>.
- 公益社団法人 日本化学会の論文
著者
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Sakamoto Shuichi
Institute for Drug Discovery Research, Yamanouchi Pharmaceutical Co., Ltd.,
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Tsuchiya Tsutomu
Institute of Bioorganic Chemistry
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Umezawa Sumio
Institute of Bioorganic Chemistry
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Sakamoto Shuichi
Institute of Bioorganic Chemistry
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Kajikawa Norio
Institute of Bioorganic Chemistry
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