Ns-Trp-OAllyl | 853245-44-0

• 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: Ns-Trp-OAllyl
• 英文别名: prop-2-enyl (2S)-3-(1H-indol-3-yl)-2-[(2-nitrophenyl)sulfonylamino]propanoate
• CAS: 853245-44-0
• 化学式: C₂₀H₁₉N₃O₆S
• 分子量: 429.453
• InChiKey: AMYALERLNANDPA-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  143
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Ns-Trp-OAllyl 在 三异丙基硅烷 、 碳酸氢钠 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 、 水 为溶剂， 反应 26.0h， 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：

  L-色氨酸 在 对甲苯磺酸 、 三乙胺 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 5.5h， 生成 Ns-Trp-OAllyl
  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

• WO2023/152347
  申请人：——

  公开号：——

  公开（公告）日：——
• 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.