(S)-3-[2-((R)-2-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-ethylsulfanyl)-1H-indol-3-yl]-2-(2-nitro-benzenesulfonylamino)-propionic acid allyl ester | 853245-45-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (S)-3-[2-((R)-2-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-ethylsulfanyl)-1H-indol-3-yl]-2-(2-nitro-benzenesulfonylamino)-propionic acid allyl ester
• 英文别名: prop-2-enyl (2S)-3-[2-[(2R)-3-[(2-methylpropan-2-yl)oxy]-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-oxopropyl]sulfanyl-1H-indol-3-yl]-2-[(2-nitrophenyl)sulfonylamino]propanoate
• CAS: 853245-45-1
• 化学式: C₃₂H₄₀N₄O₁₀S₂
• 分子量: 704.822
• InChiKey: FAEKRIKIUWXLGS-ZEQRLZLVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.9
• 重原子数：
  48
• 可旋转键数：
  18
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.41
• 拓扑面积：
  232
• 氢给体数：
  3
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  (S)-3-[2-((R)-2-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-ethylsulfanyl)-1H-indol-3-yl]-2-(2-nitro-benzenesulfonylamino)-propionic acid allyl ester 在 三异丙基硅烷 、 三氟乙酸 作用下， 以 二氯甲烷 、 水 为溶剂， 反应 24.0h， 生成 (R)-3-{3-[(S)-2-Allyloxycarbonyl-2-(2-nitro-benzenesulfonylamino)-ethyl]-1H-indol-2-ylsulfanyl}-2-amino-propionic acid
  参考文献：
  名称：

  A Solid-Phase Approach to the Phallotoxins:  Total Synthesis of [Ala⁷]-Phalloidin

  摘要：

  [GRAPHICS]Herein we report a solid-phase synthetic approach to [Ala(7)]-phalloidin (1). Prior syntheses of phallotoxins were carried out using solution-phase routes that required large scale and preclude library production. The route presented here consists of solution-phase preparation of key orthogonally protected amino acid building blocks, followed by a solid-phase peptide synthesis sequence, featuring two resin-bound macro-cyclization reactions. The final product mixture was composed of two atropisomeric compounds, one designated "natural" (1) and the other designated "non-natural" W). The structures of these species were modeled using restrained energy minimization with NMR-derived restraints.

  DOI：

  10.1021/jo0503153
• 作为产物：
  描述：

  (Boc-Cys-OBu^t)2 在 磺酰氯 、 碳酸氢钠 作用下， 以 氯仿 为溶剂， 反应 0.75h， 生成 (S)-3-[2-((R)-2-tert-Butoxycarbonyl-2-tert-butoxycarbonylamino-ethylsulfanyl)-1H-indol-3-yl]-2-(2-nitro-benzenesulfonylamino)-propionic acid allyl ester
  参考文献：
  名称：

  A Solid-Phase Approach to the Phallotoxins:  Total Synthesis of [Ala⁷]-Phalloidin

  摘要：

  [GRAPHICS]Herein we report a solid-phase synthetic approach to [Ala(7)]-phalloidin (1). Prior syntheses of phallotoxins were carried out using solution-phase routes that required large scale and preclude library production. The route presented here consists of solution-phase preparation of key orthogonally protected amino acid building blocks, followed by a solid-phase peptide synthesis sequence, featuring two resin-bound macro-cyclization reactions. The final product mixture was composed of two atropisomeric compounds, one designated "natural" (1) and the other designated "non-natural" W). The structures of these species were modeled using restrained energy minimization with NMR-derived restraints.

  DOI：

  10.1021/jo0503153

文献信息

• A Solid-Phase Approach to the Phallotoxins:  Total Synthesis of [Ala⁷]-Phalloidin
  作者：Marc O. Anderson、Anang A. Shelat、R. Kiplin Guy

  DOI：10.1021/jo0503153

  日期：2005.6.1

  [GRAPHICS]Herein we report a solid-phase synthetic approach to [Ala(7)]-phalloidin (1). Prior syntheses of phallotoxins were carried out using solution-phase routes that required large scale and preclude library production. The route presented here consists of solution-phase preparation of key orthogonally protected amino acid building blocks, followed by a solid-phase peptide synthesis sequence, featuring two resin-bound macro-cyclization reactions. The final product mixture was composed of two atropisomeric compounds, one designated "natural" (1) and the other designated "non-natural" W). The structures of these species were modeled using restrained energy minimization with NMR-derived restraints.