benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate | 1423738-99-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate
• CAS: 1423738-99-1
• 化学式: C₃₀H₄₆N₄O₄
• 分子量: 526.72
• InChiKey: APCOSNYMGCGGAD-MHZLTWQESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.34
• 重原子数：
  38.0
• 可旋转键数：
  19.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  113.39
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate 在 三苯基膦 、 水 作用下， 以 四氢呋喃 为溶剂， 反应 1.0h， 生成
  参考文献：
  名称：

  A practical route to long-chain non-natural α,ω-diamino acids

  摘要：

  An efficient method for the synthesis of long-chain alpha,omega-diamino acids, starting from natural alpha-amino acids, has been developed. The long-chain skeleton has been generated through condensation between a protected aldehyde, derived from l-aspartic acid, and an ylide obtained from an omega-hydroxy-alkyl phosphonium salt. After conversion of the omega-hydroxy group into an amine, catalytic hydrogenation produced the N,N'-protected alpha,omega-diamino acid. The present route to alpha,omega-diamino acids allows the modulation of the chain length depending on the length of the ylide used for the Wittig olefination reaction.

  DOI：

  10.1007/s00726-012-1349-0
• 作为产物：
  描述：

  benzyl (2S,4E)-2-(tert-butoxycarbonylamino)-6-oxohex-4-enoate 在 4-二甲氨基吡啶 、 sodium azide 、 四丁基碘化铵 、 N,N-二异丙基乙胺 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 9.67h， 生成 benzyl (2S)-18-azido-2-(tert-butoxycarbonylamino)-octadeca-4,6-dienoate
  参考文献：
  名称：

  A practical route to long-chain non-natural α,ω-diamino acids

  摘要：

  An efficient method for the synthesis of long-chain alpha,omega-diamino acids, starting from natural alpha-amino acids, has been developed. The long-chain skeleton has been generated through condensation between a protected aldehyde, derived from l-aspartic acid, and an ylide obtained from an omega-hydroxy-alkyl phosphonium salt. After conversion of the omega-hydroxy group into an amine, catalytic hydrogenation produced the N,N'-protected alpha,omega-diamino acid. The present route to alpha,omega-diamino acids allows the modulation of the chain length depending on the length of the ylide used for the Wittig olefination reaction.

  DOI：

  10.1007/s00726-012-1349-0