(4S)-3-(Benzyloxy)-4-methoxy-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene | 159749-97-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (4S)-3-(Benzyloxy)-4-methoxy-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene
• 英文别名: (4S)-3-(Benzyloxy)-4-methoxy-{3-oxo-3-[2-oxo-4-(phenylmethyl)-3-oxazolidinyl]propyl}benzene；(4S)-4-benzyl-3-[3-(4-methoxy-3-phenylmethoxyphenyl)propanoyl]-1,3-oxazolidin-2-one
• CAS: 159749-97-0
• 化学式: C₂₇H₂₇NO₅
• 分子量: 445.515
• InChiKey: MBAMESBTNUTSAE-QHCPKHFHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  33
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (4S)-3-(Benzyloxy)-4-methoxy-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene 在 lithium hydroxide 、 2,4,6-三异丙基苯磺酰叠氮化物 、 双氧水 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 2.03h， 生成 (S)-2-Azido-3-<3-(benzyloxy)-4-methoxyphenyl>propionic acid
  参考文献：
  名称：

  A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis

  摘要：

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.

  DOI：

  10.1021/jo00088a009
• 作为产物：
  描述：

  3-羟基-4-甲氧基肉桂酸 在 palladium on activated charcoal 氢氧化钾 、 正丁基锂 、 氢气 、 potassium carbonate 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 丙酮 为溶剂， 反应 39.42h， 生成 (4S)-3-(Benzyloxy)-4-methoxy-<3-oxo-3-<2-oxo-4-(phenylmethyl)-3-oxazolidinyl>propyl>benzene
  参考文献：
  名称：

  A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis

  摘要：

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.

  DOI：

  10.1021/jo00088a009

文献信息

• A Formal Total Synthesis of the ACE Inhibitor K-13. An Application of Arene-Ruthenium Chemistry to Complex Chemical Synthesis
  作者：Anthony J. Pearson、Kieseung Lee

  DOI：10.1021/jo00088a009

  日期：1994.5

  Stoichiometric ruthenium activation of 4-chlorophenylalanine derivatives toward nucleophilic substitution, using phenoxide nucleophiles that are derived from protected dipeptides, allowed the formation of isodityrosine derivatives that are synthetic precursors to the ACE inhibitor K-13. An evaluation of carboxyl blocking groups revealed that a 2-bromoethyl ester is the most useful in terms of its compatibility with ruthenium complexation and subsequent nucleophile addition but that its removal is problematic. Conversion to iodoethyl ester using Finkelstein reaction conditions, in the presence of the peptide and amino acid functionality, provided a solution to this problem, since the iodoethyl group was easily removed on treatment with samarium diiodide.