(4S,5R)-4,5-dihydro-2-phenyl-4-carboethoxy-5-benzyl-1,3-oxazole | 869103-47-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S,5R)-4,5-dihydro-2-phenyl-4-carboethoxy-5-benzyl-1,3-oxazole
• 英文别名: ethyl (4R,5S)-4-benzyl-2-phenyl-4,5-dihydro-1,3-oxazole-5-carboxylate
• CAS: 869103-47-9
• 化学式: C₁₉H₁₉NO₃
• 分子量: 309.365
• InChiKey: TUZQDLYULXAPQJ-SJORKVTESA-N

物化性质

• 沸点：
  443.4±38.0 °C(Predicted)
• 密度：
  1.15±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  23
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  47.9
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (4S,5R)-4,5-dihydro-2-phenyl-4-carboethoxy-5-benzyl-1,3-oxazole 在 盐酸 作用下， 以 乙醇 、 水 为溶剂， 反应 8.0h， 生成 (2S,3R)-3-氨基-2-羟基-4-苯丁酸
  参考文献：
  名称：

  Chemoenzymatic formal total synthesis of (−)-bestatin

  摘要：

  A highly stereoselective, enzymatic reduction of an alpha-chloro-beta-keto ester provided the key intermediate for a total synthesis of the alpha-hydroxy-beta-amino acid moiety of (-)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.022
• 作为产物：
  描述：

  4-苯基乙酰乙酸乙酯 在 KPi buffer 、 XAD-4 resin 磺酰氯 、 air 、 葡萄糖 、 Escherichia coli BL₂₁(DE₃)(pIK₄) overexpressing reductase 、 三氟化硼乙醚 、 potassium carbonate 作用下， 以 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.0h， 生成 (4S,5R)-4,5-dihydro-2-phenyl-4-carboethoxy-5-benzyl-1,3-oxazole
  参考文献：
  名称：

  Chemoenzymatic formal total synthesis of (−)-bestatin

  摘要：

  A highly stereoselective, enzymatic reduction of an alpha-chloro-beta-keto ester provided the key intermediate for a total synthesis of the alpha-hydroxy-beta-amino acid moiety of (-)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule. (C) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2005.08.022

文献信息

• Chemoenzymatic formal total synthesis of (−)-bestatin
  作者：Brent D. Feske、Jon D. Stewart

  DOI：10.1016/j.tetasy.2005.08.022

  日期：2005.9

  A highly stereoselective, enzymatic reduction of an alpha-chloro-beta-keto ester provided the key intermediate for a total synthesis of the alpha-hydroxy-beta-amino acid moiety of (-)-bestatin. The reduction product was cyclized to a glycidic ester that was opened in a Ritter reaction with benzonitrile, affording a trans-oxazoline, which was hydrolyzed under acidic conditions to the target molecule. (C) 2005 Elsevier Ltd. All rights reserved.