α-FMOC-γ-BOC-L-Orn-3(CBZ).3(CBZ) | 156743-08-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: α-FMOC-γ-BOC-L-Orn-3(CBZ).3(CBZ)
• CAS: 156743-08-7
• 化学式: C₄₇H₅₇N₅O₉
• 分子量: 835.998
• InChiKey: VPIPZSZZVQEKPB-RWYGWLOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.66
• 重原子数：
  61.0
• 可旋转键数：
  20.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  173.63
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  α-FMOC-γ-BOC-L-Orn-3(CBZ).3(CBZ) 在 哌啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 以97%的产率得到((S)-4-Amino-4-{3-[benzyloxycarbonyl-(3-benzyloxycarbonylamino-propyl)-amino]-propylcarbamoyl}-butyl)-carbamic acid tert-butyl ester
  参考文献：
  名称：

  Practical synthesis of the putative polyamine spider toxin FTX: a proposed blocker of voltage-sensitive calcium channels

  摘要：

  FTX (FTX-3.3), a putative polyamine toxin from American funnel-web spiders, has been synthesized from tri-CBZ-L-arginine. Raney nickel mediated desulfurization of a thioamide, generated selectively with Lawesson's reagent in the presence of the benzyloxycarbamates, allowed ready access to the S-enantiomer. The synthetic sample with the claimed structure for FTX-3.3 differs spectroscopically from the data published for the isolated toxin. The published structure requires a reappraisal of the spectroscopic data.

  DOI：

  10.1016/s0040-4039(00)73048-6
• 作为产物：
  描述：

  叔丁氧羰基-3,3'-亚氨基二丙胺 在 sodium hydroxide 、 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 生成 α-FMOC-γ-BOC-L-Orn-3(CBZ).3(CBZ)
  参考文献：
  名称：

  Practical synthesis of the putative polyamine spider toxin FTX: a proposed blocker of voltage-sensitive calcium channels

  摘要：

  FTX (FTX-3.3), a putative polyamine toxin from American funnel-web spiders, has been synthesized from tri-CBZ-L-arginine. Raney nickel mediated desulfurization of a thioamide, generated selectively with Lawesson's reagent in the presence of the benzyloxycarbamates, allowed ready access to the S-enantiomer. The synthetic sample with the claimed structure for FTX-3.3 differs spectroscopically from the data published for the isolated toxin. The published structure requires a reappraisal of the spectroscopic data.

  DOI：

  10.1016/s0040-4039(00)73048-6