(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-oxy-5-tetradecyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester | 136705-44-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-oxy-5-tetradecyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester
• CAS: 136705-44-7
• 化学式: C₂₆H₅₁NO₅Si
• 分子量: 485.78
• InChiKey: QRPOVVBYDLVRIN-ISKFKSNPSA-N

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-oxy-5-tetradecyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester 在 三甲氧基磷 作用下， 以92%的产率得到(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-tetradecyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of 3-(ethoxycarbonyl)-4-hydroxy-2-isoxazoline-2-oxides. A new approach to the synthesis of 4-hydroxylated 2-isoxazolines

  摘要：

  Treatment of 2-bromo aldehydes and ethyl nitroacetate with alumina without solvent, or in solution with a tertiary base, at room temperature gives the diastereoisomeric title compounds in fair yields by a tandem nitroaldol reaction-cyclization sequence opening a new route for the preparation of trans and cis 4-hydroxylated 2-isoxazolines in a predictable way.

  DOI：

  10.1021/jo00022a005
• 作为产物：
  描述：

  (4S,5R)-4-Hydroxy-2-oxy-5-tetradecyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester 、 叔丁基二甲基氯硅烷 在 咪唑 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以99%的产率得到(4S,5R)-4-(tert-Butyl-dimethyl-silanyloxy)-2-oxy-5-tetradecyl-4,5-dihydro-isoxazole-3-carboxylic acid ethyl ester
  参考文献：
  名称：

  Stereocontrolled synthesis of 3-(ethoxycarbonyl)-4-hydroxy-2-isoxazoline-2-oxides. A new approach to the synthesis of 4-hydroxylated 2-isoxazolines

  摘要：

  Treatment of 2-bromo aldehydes and ethyl nitroacetate with alumina without solvent, or in solution with a tertiary base, at room temperature gives the diastereoisomeric title compounds in fair yields by a tandem nitroaldol reaction-cyclization sequence opening a new route for the preparation of trans and cis 4-hydroxylated 2-isoxazolines in a predictable way.

  DOI：

  10.1021/jo00022a005