(3S,4R,E)-5-(benzyloxy)-4-nitro-1-phenylpent-1-en-3-ol | 1612257-15-4

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂醇
• 英文名称: (3S,4R,E)-5-(benzyloxy)-4-nitro-1-phenylpent-1-en-3-ol
• 英文别名: (E,3S,4R)-4-nitro-1-phenyl-5-phenylmethoxypent-1-en-3-ol
• CAS: 1612257-15-4
• 化学式: C₁₈H₁₉NO₄
• 分子量: 313.353
• InChiKey: VKLZJOUIXSDYSD-HGFSOSMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  23
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  75.3
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3S,4R,E)-5-(benzyloxy)-4-nitro-1-phenylpent-1-en-3-ol 在 2,6-二甲基吡啶 、 indium 、 sodium hydride 、 碳酸氢钠 、 氯化铵 、 溶剂黄146 、 锌 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 21.5h， 生成 (2R,3S,E)-1-(benzyloxy)-3-((tert-butyldimethylsilyl)oxy)-N-methyl-5-phenylpent-4-en-2-amine
  参考文献：
  名称：

  Catalytic Asymmetric Total Synthesis of (+)-Caprazol

  摘要：

  Catalytic asymmetric total synthesis of caprazol, a lipo-nucleoside antibiotic, has been accomplished employing two of the stereoselective C-C bond forming reactions as key transformations. The stereochemistries of the β-hydroxy-α-aminoester moiety at the juncture of the uridine part and diazepanone part, and of the β-hydroxy-α-amino acid moiety embedded in the diazepanone system, were constructed using a diastereoselective isocyanoacetate aldol reaction (dr = 88:12) and an enantioselective anti-nitroaldol reaction catalyzed by a Nd/Na-chiral amide ligand (dr = 12:1, 95% ee), respectively.

  DOI：

  10.1021/ol501397b
• 作为产物：
  描述：

  反式肉桂醛 、 1-benzyloxy-2-nitroethane 在 Nd⁽³⁺⁾*0.2O^(2-)*2.6C₃H₇O^(1-) 、 C₁₉H₁₈F₂N₂O₄ 、 sodium hexamethyldisilazane 作用下， 以 四氢呋喃 为溶剂， 反应 120.0h， 以84.615%的产率得到
  参考文献：
  名称：

  Catalytic Asymmetric Total Synthesis of (+)-Caprazol

  摘要：

  Catalytic asymmetric total synthesis of caprazol, a lipo-nucleoside antibiotic, has been accomplished employing two of the stereoselective C-C bond forming reactions as key transformations. The stereochemistries of the β-hydroxy-α-aminoester moiety at the juncture of the uridine part and diazepanone part, and of the β-hydroxy-α-amino acid moiety embedded in the diazepanone system, were constructed using a diastereoselective isocyanoacetate aldol reaction (dr = 88:12) and an enantioselective anti-nitroaldol reaction catalyzed by a Nd/Na-chiral amide ligand (dr = 12:1, 95% ee), respectively.

  DOI：

  10.1021/ol501397b

文献信息

• Catalytic Asymmetric Total Synthesis of (+)-Caprazol
  作者：Purushothaman Gopinath、Lu Wang、Hikaru Abe、Gandamala Ravi、Takashi Masuda、Takumi Watanabe、Masakatsu Shibasaki

  DOI：10.1021/ol501397b

  日期：2014.6.20

  Catalytic asymmetric total synthesis of caprazol, a lipo-nucleoside antibiotic, has been accomplished employing two of the stereoselective C-C bond forming reactions as key transformations. The stereochemistries of the β-hydroxy-α-aminoester moiety at the juncture of the uridine part and diazepanone part, and of the β-hydroxy-α-amino acid moiety embedded in the diazepanone system, were constructed using a diastereoselective isocyanoacetate aldol reaction (dr = 88:12) and an enantioselective anti-nitroaldol reaction catalyzed by a Nd/Na-chiral amide ligand (dr = 12:1, 95% ee), respectively.