A facile synthesis of anomeric methyl DL-tolyposaminides, methyl DL-forosaminides, and related substances.

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概要

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• The reaction of β-nitro alcohols (2-nitroethanol, 1-nitro-2-propanol, and 1-nitro-2-butanol) with acrylaldehyde in the presence of diethylamine-formic acid gave anomeric mixture of 4-nitro-DL-pento-, hexo-, and heptopyranoses (<B>5</B>) in reasonable yields. <B>5</B> were converted to the corresponding methyl 4-amino-DL-pento-, hexo-, and heptopyranosides (<B>8</B>) by <I>O</I>-methylation followed by reduction. Anomeric methyl DL-tolyposaminides and DL-forosaminides were synthesized in a good yield from anomeric methyl 4-nitro-2,3,4,6-tetradeoxy-DL-<I>erythro</I>-hexopyranosides (<B>6b</B><SUB>1</SUB> and <B>6b</B><SUB>2</SUB>). The configuration of methyl 4-nitro-DL-hexo-, and heptopyranosides (<B>6b</B> and <B>6c</B>) and methyl 4-acetamido-DL-hexo- and heptopyranosides (<B>8b</B> and <B>8c</B>) was established on the basis of PMR data.

• 公益社団法人 日本化学会の論文

著者

• Kaji Eisuke

  School Of Pharmaceutical Sciences Kitasato University

• Zen Shonosuke

  School Of Pharmaceutical Sciences Kitasato University

• Kohno Haruo

  School of Pharmaceutical Sciences, Kitasato University

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• A facile synthesis of anomeric methyl DL-tolyposaminides, methyl DL-forosaminides, and related substances.

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