(4R,5R)-trans-N-[3'-(diethoxyphosphoryl)propionyl]hexahydro-benzoxazolidin-2-one | 909282-36-6

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 有机膦酸及其衍生物
• 英文名称: (4R,5R)-trans-N-[3'-(diethoxyphosphoryl)propionyl]hexahydro-benzoxazolidin-2-one
• 英文别名: (3aR,7aR)-3-(3-diethoxyphosphorylpropanoyl)-3a,4,5,6,7,7a-hexahydro-1,3-benzoxazol-2-one
• CAS: 909282-36-6
• 化学式: C₁₄H₂₄NO₆P
• 分子量: 333.321
• InChiKey: LQNLIUVVSWISDK-VXGBXAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  22
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.86
• 拓扑面积：
  82.1
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (4R,5R)-trans-N-[3'-(diethoxyphosphoryl)propionyl]hexahydro-benzoxazolidin-2-one 在 sodium hexamethyldisilazane 、 2,4,6-三异丙基苯磺酰叠氮化物 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 以66%的产率得到(4R,5R)-trans-N-[3'-(diethoxyphosphoryl)-2'(S)-azidopropionyl]hexahydro-benzoxazolidin-2-one
  参考文献：
  名称：

  Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one

  摘要：

  N-Acylation of readily available, enantiopure oxazolidinone (4R,5R)-1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4R,5R)-2 and (4R,5R)-7, respectively, which are azidated with high diastereoselectivity by means of the reaction between their sodium enolates (4R,5R)-2-Na and (4R,5R)-7-Na with trisyl azide. Removal of the chiral auxiliary from azidated products (4R,5R,2'S)-3 and (4R,5R,2'R)-8 followed by hydrogenation and hydrolysis of the resulting carboxylic acids (S)-4 and (R)-9 gave the pharmacologically relevant aminophosphonic acids (S)-AP-3 and (R)-AP-4 in good yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.018
• 作为产物：
  描述：

  (2-chlorocarboxyethyl)phosphonic acid diethyl ester 、 trans-hexahydrobenzoxazolidin-2-one 在 正丁基锂 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 4.0h， 以82%的产率得到(4R,5R)-trans-N-[3'-(diethoxyphosphoryl)propionyl]hexahydro-benzoxazolidin-2-one
  参考文献：
  名称：

  Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one

  摘要：

  N-Acylation of readily available, enantiopure oxazolidinone (4R,5R)-1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4R,5R)-2 and (4R,5R)-7, respectively, which are azidated with high diastereoselectivity by means of the reaction between their sodium enolates (4R,5R)-2-Na and (4R,5R)-7-Na with trisyl azide. Removal of the chiral auxiliary from azidated products (4R,5R,2'S)-3 and (4R,5R,2'R)-8 followed by hydrogenation and hydrolysis of the resulting carboxylic acids (S)-4 and (R)-9 gave the pharmacologically relevant aminophosphonic acids (S)-AP-3 and (R)-AP-4 in good yield. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2006.06.018

文献信息

• Enantioselective synthesis of (S)-2-amino-3-phosphonopropionic acid, (S)-AP-3, and (R)-2-amino-4-phosphonobutanoic acid, (R)-AP-4, via diastereoselective azidation of (4R,5R)-trans-N-[(diethoxyphosphoryl)propionyl]- and (4R,5R)-trans-N-[(diethoxyphosphoryl)butanoyl]hexahydrobenzoxazolidin-2-one
  作者：Gloria Reyes-Rangel、Virginia Marañón、C. Gabriela Avila-Ortiz、Cecilia Anaya de Parrodi、Leticia Quintero、Eusebio Juaristi

  DOI：10.1016/j.tet.2006.06.018

  日期：2006.8

  N-Acylation of readily available, enantiopure oxazolidinone (4R,5R)-1b with (diethoxyphosphoryl)propionyl chloride and (diethoxyphosphoryl)butanoyl chloride affords de title substrates (4R,5R)-2 and (4R,5R)-7, respectively, which are azidated with high diastereoselectivity by means of the reaction between their sodium enolates (4R,5R)-2-Na and (4R,5R)-7-Na with trisyl azide. Removal of the chiral auxiliary from azidated products (4R,5R,2'S)-3 and (4R,5R,2'R)-8 followed by hydrogenation and hydrolysis of the resulting carboxylic acids (S)-4 and (R)-9 gave the pharmacologically relevant aminophosphonic acids (S)-AP-3 and (R)-AP-4 in good yield. (c) 2006 Elsevier Ltd. All rights reserved.