Aminosugars. XXIII. L-Idofuranose Derivatives Containing a Heterocycle at <I>C</I>-5,6 Position

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概要

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• 2-Aryl-(5<I>S</I>)- and -(4<I>S</I>)-(3′-<I>O</I>-benzyl- and 3′-<I>O</I>-methyl-1′,2′-<I>O</I>-isopropylklene-α-D-xylo-tetrofuranos-4′-yl)-2-oxazolines (<B>3</B> and <B>7</B>) were prepared from 6-aroylamido-6-deoxy-5-<I>O</I>-tosyl-D-glucofuranose and 5,6-aroylepimino-5,6-dideoxy-L-idofuranose derivatives, respectively. The corresponding 2-thioxo-(4<I>R</I>)- and -(5<I>S</I>)-thiazolidine derivatives (<B>11</B> and <B>13</B>) were also synthesized from 5,6-dideoxy-5,6-epimino-L-idofuranose and 6-azido-6-deoxy 5-<I>O</I>-tosyl-D-glucofuranose derivatives, respectively. 2-S-Methylated derivatives of <B>11</B> and <B>13</B> were reduced with aluminum amalgam to give the corresponding (4<I>R</I>)- and (5<I>S</I>)-thiazolidine derivatives, respectively. Formation of an intramolecular hemiaminal ring in <B>11</B> gave a new type of bicyclic derivatives; (5<I>S</I>,6<I>R</I>,8<I>R</I>)-triacetoxy-(7<I>S</I>)-substituted-2-thioxo-(8a<I>R</I>)-perhydropyrido[1,2-<I>c</I>]thiazole (<B>16a</B> and <B>16b</B>). The structure of new compounds was examined by NMR spectroscopy.

• 公益社団法人 日本化学会の論文

著者

• Yoshimura Juji

  Laboratorium für Organische Chemie Technische Hochschule Tokyo

• Iwakawa Masaharu

  Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology

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