Synthesis of a chiral .ALPHA.-(aminooxy)arylacetic ester. II. A route through a chiral 2-hydroxy-2-phenylacetic acid derivative.
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概要
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A simple and practical synthetic route has been developed for the synthesis of a chiral α-(aminooxy) ester (<I>S</I>)-<B>16</B>, which is a synthetic intermediate for a potent antipseudomonal cephalosporin antibiotic M-14659. In this synthetic route, the key intermediate is α-hydroxy acid (<I>R</I>)-<B>7</B> (100%ee), which is prepared by an asymmetric reduction of α-keto ester with NaBH<SUB>4</SUB>-(<I>R</I>,<I>R</I>)-tartaric acid followed by a hydrolysis and an optical resolution using L-Leu–NHNH<SUB>2</SUB>. (<I>S</I>)-<B>16</B> is obtained stereoselectively through 3 steps from (<I>R</I>)-<B>7</B>. HPLC analyses and NMR studies have proved that the (<I>S</I>)-<B>16</B> thus prepared is completely optically pure.
- 公益社団法人 日本化学会の論文
著者
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Iwagami Hisao
Central Research Laboratories Of Ajinomoto Co. Inc.
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Honda Yutaka
Central Research Laboratories, Ajinomoto Co., Inc.
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Yatagai Masanobu
Central Research Laboratories, Ajinomoto Co., Inc.
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Nakazawa Masakazu
Central Research Laboratories, Ajinomoto Co., Inc.
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Orita Haruo
Central Research Laboratories, Ajinomoto Co., Inc.
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Ohnuki Takashi
Central Research Laboratories, Ajinomoto Co., Inc.
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Yukawa Toshihide
Central Research Laboratories, Ajinomoto Co., Inc.
関連論文
- Optimal Conditions for the Enzymatic Production of L-Aromatic Amino Acids from the Corresponding 5-Substituted Hydantoins(Microbiology & Fermentation Industry)
- Synthesis of a chiral .ALPHA.-(aminooxy)arylacetic ester. II. A route through a chiral 2-hydroxy-2-phenylacetic acid derivative.
- Synthesis of a chiral .ALPHA.-(aminooxy)arylacetic ester. I. A route through optical resolution of a racemic .ALPHA.-(phthalimidooxy)arylacetic acid.