Inositol Derivatives. V. Selective Benzoylation of 1,2-<I>O</I>-Cyclohexylidene-<I>myo</I>-inositol and Preparation of New <I>O</I>-<I>p</I>-Tolylsulfonyl-<I>myo</I>-inositols
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概要
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The reaction of l,2-<I>O</I>-cyclohexylidene-<I>myo</I>-inositol (<B>1a</B>) with 1.5 equiv. of benzoyl chloride below 0°C gave 3-<I>O</I>-benzoate (<B>2a</B>) predominantly in 40% yield, together with easily separable 3,6-di-<I>O</I>-benzoate (<B>3a</B>) in 2.5% yield. Selective sulfonylation of <B>2a</B> gave three new <I>O</I>-<I>p</I>-tolylsulfonyl-<I>myo</I>-inositols (the 4,6- (<B>8a</B>), 4,5- (<B>9a</B>), and 4,5,6-<I>p</I>-toluenesulfonates (<B>10</B>)). From <B>3a</B>, two <I>O</I>-<I>p</I>-tolylsulfonyl derivatives (5- (<B>15a</B>) and 4,5-<I>p</I>-toluenesulfonates (<B>16</B>)) were obtained. The relative reactivities, toward benzoylation, of the hydroxyl groups of <B>1a</B> were shown to be almost similar to those observed in tosylation. The <I>p</I>-tolylsulfonyloxy function on C–5 of <B>10</B> was found to be readily displaced preferentially by chloride ion.
- 公益社団法人 日本化学会の論文
著者
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Oki Shuichi
Department Of Neurosurgery Hiroshima City Asa Hospital
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Ogawa Seiichiro
Department Of Applied Cemistry Faculty Of Science And Technology Keio University
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Suami Tetsuo
Department of Applied Chemistry Faculty of Engineering Keio University
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Ohashi Kumiko
Department of Applied Chemistry, Faculty of Engineering, Keio University
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Oki Shuichi
Department of Applied Chemistry, Faculty of Engineering, Keio University
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