(3S)-N-benzyloxycarbonyl-3-amino-2-hydroxy-1-nitro-4-phenylbutane | 187942-94-5

• 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: (3S)-N-benzyloxycarbonyl-3-amino-2-hydroxy-1-nitro-4-phenylbutane
• CAS: 187942-94-5
• 化学式: C₁₈H₂₀N₂O₅
• 分子量: 344.367
• InChiKey: VVNDYKGBEUVPRU-BHWOMJMDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.16
• 重原子数：
  25.0
• 可旋转键数：
  8.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  101.7
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (3S)-N-benzyloxycarbonyl-3-amino-2-hydroxy-1-nitro-4-phenylbutane 在 4-二甲氨基吡啶 、 sodium tetrahydroborate 作用下， 以 乙醚 、 乙醇 为溶剂， 反应 4.0h， 生成 (3S)-N-benzyloxycarbonyl-3-amino-1-nitro-4-phenylbutane
  参考文献：
  名称：

  A Mild Multistep Conversion of N-Protected α-Amino Acids into N-Protected β3-Amino Acids Utilizing the Nef Reaction

  摘要：

  Current methods of homologation of alpha-amino acids to beta-amino acids have limitations. To overcome these shortfalls the Nef reaction has been utilized in the multistep synthesis of beta(3)-amino acids from alpha-amino acids. In this approach, N-protected amino aldehydes, easily accessed from alpha-amino acids, were transformed into the N-protected.gamma-amino nitroalkanes. The Nef reaction was then used to smoothly convert the nitroalkanes into the corresponding N-protected beta(3)-amino acids without notable racemization.

  DOI：

  10.1055/s-0032-1318344
• 作为产物：
  描述：

  Z-L-苯丙氨醇 在 potassium fluoride 、 草酰氯 、 二甲基亚砜 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 8.67h， 生成 (3S)-N-benzyloxycarbonyl-3-amino-2-hydroxy-1-nitro-4-phenylbutane
  参考文献：
  名称：

  A Mild Multistep Conversion of N-Protected α-Amino Acids into N-Protected β3-Amino Acids Utilizing the Nef Reaction

  摘要：

  Current methods of homologation of alpha-amino acids to beta-amino acids have limitations. To overcome these shortfalls the Nef reaction has been utilized in the multistep synthesis of beta(3)-amino acids from alpha-amino acids. In this approach, N-protected amino aldehydes, easily accessed from alpha-amino acids, were transformed into the N-protected.gamma-amino nitroalkanes. The Nef reaction was then used to smoothly convert the nitroalkanes into the corresponding N-protected beta(3)-amino acids without notable racemization.

  DOI：

  10.1055/s-0032-1318344