Aminocyclitols. XXVIII. Bromination of Inosamines and Inosadiamines

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概要

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• Bromination of four inosamines (<I>myo</I>-2 (<B>1</B>), <I>chiro</I>-1 (<B>2</B>), <I>muco</I>-1 (<B>3</B>), and <I>scyllo</I> (<B>4</B>)) and three inosadiamines (<I>neo</I>-1,4 (<B>11</B>), <I>muco</I>-1,5 (<B>14a,b</B>), and <I>muco</I>-1,4 (<B>19</B>)) with acetyl bromide and acetic anhydride in a sealed tube at 130–160°C has been studied. 2,5-Dibromo-2,5-dideoxy-<I>chiro</I>-inosamine-3 tetraacetate (<B>8</B>), was obtained from <B>1,2</B>, and <B>3</B>, and, as a monobromide, only 2-bromo-2-deoxy-<I>chiro</I>-inosamine-3 pentaacetate (<B>7</B>) could be isolated from the bromination product of <B>3</B>. From <B>11</B>, monobromide (<B>12</B>) and dibromide (<B>13</B>) were obtained. From <B>14a</B> or <B>14b</B>, 2-bromo-2-deoxy-<I>chiro</I>-inosadiamine-3,5 pentaacetate (<B>15</B>) was obtained, and, under a more drastic condition, <B>15</B> was further brominated to afford 1,5-dibromo-1,5-dideoxy-<I>chiro</I>-inosadiamine-2,4 tetraacetate (<B>16</B>). The bromo compounds so obtained were converted into the corresponding deoxy or dideoxy derivatives by hydrogenolysis. All the structures of the new compounds have been confirmed on the basis of proton magnetic resonance (PMR) spectroscopy using their acetyl derivatives. Considering from the structures of the bromides, a mechanism of a bromination reaction has been proposed.

• 公益社団法人 日本化学会の論文

著者

• Ogawa Seiichiro

  Department Of Applied Cemistry Faculty Of Science And Technology Keio University

• Suami Tetsuo

  Department of Applied Chemistry Faculty of Engineering Keio University

• Nojima Kazuhiro

  Department of Applied Chemistry, Faculty of Engineering, Keio University

• Yanagida Shinichi

  Department of Applied Chemistry, Faculty of Engineering, Keio University

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