Branched-chain Sugars. IV. Synthesis of 5,6-Dideoxy-5-<I>C</I>-hydroxymethyl-1,2-<I>O</I>-isopropylidene-6-<I>C</I>-nitro-3-<I>O</I>-substituted-α-D-glucose Derivatives
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概要
- 論文の詳細を見る
Addition of nitryl iodide to 5-deoxy-1,2,<I>O</I>-isopropylidene-3-<I>O</I>-methyl-5-<I>C</I>-methylene-6-<I>O</I>-substituted-α-D-<I>xylo</I>-hexofuranoses (<B>3</B> and <B>4</B>), and subsequent hydrogenation with sodium borohydride gave a mixture of the corresponding 5,6-dideoxy-5-<I>C</I>-hydroxymethyl-6-<I>C</I>-nitro derivatives of D-<I>gluco</I> and L-<I>ido</I> forms. The configuration of both isomers were determined by intramolecular cyclization into the corresponding nitrocyclohexanetetrols. The ratios of D-<I>gluco</I> to L-<I>ido</I> product were 1: 2 in the case of 6-<I>O</I>-trityl derivative (<B>3</B>) and 4: 5 in the case of 6-<I>O</I>-benzyl derivative (<B>4</B>), respectively.
- 公益社団法人 日本化学会の論文
著者
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Funabashi Masuo
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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Yoshimura Juji
Laboratorium für Organische Chemie Technische Hochschule Tokyo
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Wakai Hiroo
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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Iida Takao
Laboratory of Chemistry for Natural Products, Faculty of Science, Tokyo Institute of Technology
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