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The Chan rearrangement is a chemical reaction that involves rearranging an acyloxy acetate (1) in the presence of a strong base to a 2-hydroxy-3-keto-ester (2). This procedure was employed in the Holton Taxol total synthesis.

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  • The Chan rearrangement is a chemical reaction that involves rearranging an acyloxy acetate (1) in the presence of a strong base to a 2-hydroxy-3-keto-ester (2). This procedure was employed in the Holton Taxol total synthesis. (en)
  • Die Chan-Umlagerung ist eine chemische Reaktion, die von entdeckt wurde. Es ist eine Umlagerungsreaktion von einem Acyloxacetat zu einem 2-Hydroxy-3-ketoester. (de)
  • Penataan ulang Chan merupakan sebuah reaksi kimia yang melibatkan penataan ulang sebuah alkoksi asetat (1) dengan keberadaan basa kuat menjadi 2-hidroksi-3-keto-ester (2). Prosedur ini ditemukan kembali dan digunakan pada . (in)
  • Il riarrangiamento di Chan è una reazione chimica che comporta una riorganizzazione di un acilossi acetato (1) in presenza di una base forte a un 2-idrossi-3-cheto-estere (2). Il riarrangiamento di Chan Questa procedura è stata riscoperta e utilizzata nella . (it)
  • O Rearranjo de Chan é uma reação de transposição onde ocorre o rearranjo do acetato de aciloxi (i), na presença de uma base forte, em 2-hidroxi-3-ceto-éster (ii). Inicialmente observou-se que quando o composto (i) foi tratado com dois equivalentes de di-isopropilamida de lítio (LDA) em THF verificou-se que o produto era 2-hidroxi-3-cetoésteres de etila (ii) em 52-65% de rendimento após a cromatografia. (pt)
  • 陈氏重排反应(Chan rearrangement)是一个较新的重排反应,1984年由加拿大麦吉尔大学的所发现。反应中,α-乙酸酯(1)在强碱作用下重排得到2-羟基-3-酮酯(2)。 Holton等人在合成紫杉醇时利用了该反应。 反应机理如下: 非亲核碱(如四甲基哌啶锂或二异丙基氨基锂)作用下,邻近羰基和醚氧原子的亚甲基氢脱去,生成负离子对酰氧基的羰基发生,生成一个不稳定的氧杂三元环中间体,开环,酸化即得到产物。 (zh)
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  • The Chan rearrangement is a chemical reaction that involves rearranging an acyloxy acetate (1) in the presence of a strong base to a 2-hydroxy-3-keto-ester (2). This procedure was employed in the Holton Taxol total synthesis. (en)
  • Die Chan-Umlagerung ist eine chemische Reaktion, die von entdeckt wurde. Es ist eine Umlagerungsreaktion von einem Acyloxacetat zu einem 2-Hydroxy-3-ketoester. (de)
  • Penataan ulang Chan merupakan sebuah reaksi kimia yang melibatkan penataan ulang sebuah alkoksi asetat (1) dengan keberadaan basa kuat menjadi 2-hidroksi-3-keto-ester (2). Prosedur ini ditemukan kembali dan digunakan pada . (in)
  • Il riarrangiamento di Chan è una reazione chimica che comporta una riorganizzazione di un acilossi acetato (1) in presenza di una base forte a un 2-idrossi-3-cheto-estere (2). Il riarrangiamento di Chan Questa procedura è stata riscoperta e utilizzata nella . (it)
  • O Rearranjo de Chan é uma reação de transposição onde ocorre o rearranjo do acetato de aciloxi (i), na presença de uma base forte, em 2-hidroxi-3-ceto-éster (ii). Inicialmente observou-se que quando o composto (i) foi tratado com dois equivalentes de di-isopropilamida de lítio (LDA) em THF verificou-se que o produto era 2-hidroxi-3-cetoésteres de etila (ii) em 52-65% de rendimento após a cromatografia. (pt)
  • 陈氏重排反应(Chan rearrangement)是一个较新的重排反应,1984年由加拿大麦吉尔大学的所发现。反应中,α-乙酸酯(1)在强碱作用下重排得到2-羟基-3-酮酯(2)。 Holton等人在合成紫杉醇时利用了该反应。 反应机理如下: 非亲核碱(如四甲基哌啶锂或二异丙基氨基锂)作用下,邻近羰基和醚氧原子的亚甲基氢脱去,生成负离子对酰氧基的羰基发生,生成一个不稳定的氧杂三元环中间体,开环,酸化即得到产物。 (zh)
rdfs:label
  • Chan-Umlagerung (de)
  • Chan rearrangement (en)
  • Penataan ulang Chan (in)
  • Riarrangiamento di Chan (it)
  • Rearranjo Chan (pt)
  • 陈氏重排反应 (zh)
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