(+)-erythro-2-Methylamino-1,2-diphenylethanolの絶対配位およびそのキラリティーを利用した不斉合成
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概要
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(±)-erythro-2-Methylamino-1,2-diphenylethanol was resolved by using D-10-camphorsulfonic acid, and the optically active compound (I) showing a specific rotation of +39.8°, was prepared. Compound (I) was derived from (1S, 2R)-(+)-erythro-2-amino-1,2-diphenylethanol (II) and its absolute configuration was determined as (1S, 2R). The chiral hydrazone compounds (Va and Vb) were obtained by condensation of methyl pyruvate and ethyl phenylglyoxylate with (1S, 2R)-(+)-erythro-2-(1-methyl-hydrazino)-1,2-diphenylethanol (IV). Reduction of the C=N group in these compounds was carried out using Pd-C catalyst in ethanol, followed by hydrogenolysis of the N-N linkage using the same catalyst in hydrochloroacidic ethanol solution, and hydrochlorides of amino acid ester and I were obtained. Alanine and phenylglycine formed by hydrolysis of amino acid esters afforded S configuration with optical purity of 10 and 1.9%, respectively. More than 95% of the optical purity of I was conserved during chiral amination of the ketoesters.
- 公益社団法人日本薬学会の論文
- 1979-03-25
著者
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高橋 浩
Faculty Of Pharmaceutical Science Hoshi University
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高橋 浩
星薬科大学
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富田 考一
星薬科大学
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野口 博美
星薬科大学
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乙益 寛隆
星薬科大学
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野口 博美
Hoshi Institute Of Pharmaceutical Sciences
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富田 考一
Hoshi Institute Of Pharmaceutical Sciences
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