Branched-chain deoxy nitro and amino sugar derivatives from ketose.

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概要

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• The nitromethane addition to 1,2-<I>O</I>-isopropylidene-5-<I>O</I>-trityl-α-D-<I>erythro</I>-pentofuranos-3-ulose (<B>1</B>) proceeded smoothly to give the corresponding branched-chain sugar (<B>2</B>), which on acetylation afforded (<B>3</B>) followed by elimination of acetic acid in presence of a base catalyst, resulted in the formation of the corresponding nitro olefin (<B>4</B>). The nitro olefin when subjected to borohydride reduction gave 5-<I>O</I>-acetyl-3-deoxy-1,2-<I>O</I>-isopropylidene-3-(nitromethyl)-α-D-ribofuranose (<B>5</B>), which on catalytic hydrogenation followed by acetylation yielded the 3-(acetamidomethyl)-5-<I>O</I>-acetyl-3-deoxy-1,2-<I>O</I>-isopropylidene-α-D-ribofuranose (<B>6</B>). By the study of the NMR spectra of 3-deoxy derivatives (<B>5</B>) and (<B>6</B>), their D-ribo configurations were established.

• 公益社団法人 日本化学会の論文

著者

• Abdel-Rahman M.

  Department of Chemistry, Faculty of Science, Alexandria University

関連論文

• Branched-chain deoxy nitro and amino sugar derivatives from ketose.

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