N-[(2S,3R)-2-(1-Ethoxy-ethoxy)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,3-dimethyl-4-oxo-butyl]-acetamide | 623562-16-3

• 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: N-[(2S,3R)-2-(1-Ethoxy-ethoxy)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,3-dimethyl-4-oxo-butyl]-acetamide
• 英文别名: N-[(2S,3R)-2-(1-ethoxyethoxy)-2,3-dimethyl-4-oxo-4-[(4S)-2-oxo-4-propan-2-yl-1,3-oxazolidin-3-yl]butyl]acetamide
• CAS: 623562-16-3
• 化学式: C₁₈H₃₂N₂O₆
• 分子量: 372.462
• InChiKey: OTMQRVVYTWMSSS-YMOXLXQBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  26
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-[(2S,3R)-2-(1-Ethoxy-ethoxy)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,3-dimethyl-4-oxo-butyl]-acetamide 在 lithium hydroxide 、 双氧水 作用下， 以 四氢呋喃 为溶剂， 反应 9.0h， 以93 mg的产率得到(2R,3S)-4-acetylamino-2,3-dimethyl-3-hydroxybutyric acid
  参考文献：
  名称：

  Highly diastereoselective addition of Et2AlCN to β-keto amides derived from (S)-4-isopropyl-2-oxazolidinone

  摘要：

  The addition of Et2AlCN in the presence of ZnBr2 or Et2AlCl to 1,3-dicarbonyl compounds derived from (S)-4-isopropyl-2-oxazolidinone, proceeds with high diastereoselectivity (94-98% de) and good chemical yields. This type of addition to chiral P-dicarbonyl substrates represents a new synthetic methodology leading to the formation of enantiomerically pure cyanohydrins. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.004
• 作为产物：
  描述：

  (S)-4-异丙基-3-丙酰基-2-恶唑烷酮 在 镍 正丁基锂 、 氢气 、 sodium acetate 、 4-甲基苯磺酸吡啶 、 二异丙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 甲苯 为溶剂， 反应 54.0h， 生成 N-[(2S,3R)-2-(1-Ethoxy-ethoxy)-4-((S)-4-isopropyl-2-oxo-oxazolidin-3-yl)-2,3-dimethyl-4-oxo-butyl]-acetamide
  参考文献：
  名称：

  Highly diastereoselective addition of Et2AlCN to β-keto amides derived from (S)-4-isopropyl-2-oxazolidinone

  摘要：

  The addition of Et2AlCN in the presence of ZnBr2 or Et2AlCl to 1,3-dicarbonyl compounds derived from (S)-4-isopropyl-2-oxazolidinone, proceeds with high diastereoselectivity (94-98% de) and good chemical yields. This type of addition to chiral P-dicarbonyl substrates represents a new synthetic methodology leading to the formation of enantiomerically pure cyanohydrins. (C) 2003 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2003.07.004

文献信息

• Highly diastereoselective addition of Et2AlCN to β-keto amides derived from (S)-4-isopropyl-2-oxazolidinone
  作者：Virginia Flores-Morales、Mario Fernández-Zertuche、Mario Ordóñez

  DOI：10.1016/j.tetasy.2003.07.004

  日期：2003.9

  The addition of Et2AlCN in the presence of ZnBr2 or Et2AlCl to 1,3-dicarbonyl compounds derived from (S)-4-isopropyl-2-oxazolidinone, proceeds with high diastereoselectivity (94-98% de) and good chemical yields. This type of addition to chiral P-dicarbonyl substrates represents a new synthetic methodology leading to the formation of enantiomerically pure cyanohydrins. (C) 2003 Elsevier Ltd. All rights reserved.