Synthesis of a chiral .ALPHA.-(aminooxy)arylacetic ester. I. A route through optical resolution of a racemic .ALPHA.-(phthalimidooxy)arylacetic acid.
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概要
- 論文の詳細を見る
A synthetic route has been developed to the synthesis of a chiral <I>O</I>-alkyloxime (<I>S</I>)-<B>16</B>, which can be a synthetic intermediate for a potent antipsedomonal cephalosporin antibiotic M-14659 (<B>1</B>). The oxime moiety in (<I>S</I>)-<B>16</B> has a chiral center at the carbon atom adjacent to the oxygen atom. We have achieved that (<I>S</I>)-<B>16</B> can be prepared via <I>t</I>-butyl 2-aminooxy-2-[3,4-(isopropylidenedioxy)phenyl]acetate [(<I>S</I>)-<B>15</B>] from an optically active α-(phthalimidooxy) acid (<I>S</I>)-<B>12a</B> which is obtained by resolution using quinine. It has been demostrated that M-14659 prepared from (<I>S</I>)-<B>16</B> is completely free from its (<I>R</I>)-diastereomer.
- 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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Hijiya Toyoto
Central Research Laboratories, Ajinomoto Co., Inc.
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Naora Hirokazu
Central Research Laboratories, 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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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.