Stereochemistry of nucleophilic addition reactions. VIII. Preparation of 1,5-anhydro-4,6-O-benzylidene-2,3-dideoxy-3-nitro-D-erythro-hex-2-enitol and its reactions with some nucleophiles.
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概要
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The title compound was synthesized from 1,5-anhydro-D-glucitol <I>via</I> nitromethane cyclization. The reduction of the compound with sodium borodeuteride afforded a mixture of saturated nitro compounds having an axial and equatorial deuterium atom at C-2 in an approximate ratio of 2:1. On the other hand, the reaction with hydrogen cyanide gave predominantly the adduct with the <I>manno</I> configuration, together with small amounts of a cyano olefin. The reaction with hydrazoic acid yielded addition products with the <I>gluco</I> and <I>manno</I> configurations; the ratio was strongly affected by the solvent used.
- 公益社団法人 日本化学会の論文
著者
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Nomura Yutaka
Department Of Cardiology The Center For Adult Diseases
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Sakakibara Tohru
Department Of Chemistry Yokohama City University
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Sudoh Rokuro
Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
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Nomura Yutaka
Department of Chemistry, Faculty of Science, Tokyo Institute of Technology
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