Boc-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-OBn | 376648-89-4

• 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: Boc-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-OBn
• 英文别名: benzyl (2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-5-[(2,2,2-trifluoroacetyl)amino]pentanoyl]amino]-5-[(2,2,2-trifluoroacetyl)amino]pentanoyl]amino]-5-[(2,2,2-trifluoroacetyl)amino]pentanoyl]amino]-5-[(2,2,2-trifluoroacetyl)amino]pentanoyl]amino]-5-[(2,2,2-trifluoroacetyl)amino]pentanoyl]amino]-5-[(2,2,2-trifluoroacetyl)amino]pentanoyl]amino]-5-[(2,2,2-trifluoroacetyl)amino]pentanoyl]amino]-5-[(2,2,2-trifluoroacetyl)amino]pentanoate
• CAS: 376648-89-4
• 化学式: C₆₈H₈₈F₂₄N₁₆O₁₉
• 分子量: 1889.5
• InChiKey: HTTOKACXHDNYAM-BXXNOCLASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.2
• 重原子数：
  127
• 可旋转键数：
  53
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.66
• 拓扑面积：
  501
• 氢给体数：
  16
• 氢受体数：
  43

反应信息

• 作为反应物：
  描述：

  Boc-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-OBn 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 以100%的产率得到Boc-NH-[Orn(COCF3)]8CO2H
  参考文献：
  名称：

  An Efficient, Scalable Synthesis of the Molecular Transporter Octaarginine via a Segment Doubling Strategy

  摘要：

  [GRAPHICS]Short oligomers of arginine function as remarkably efficient molecular transporters of drugs and probe molecules into cells and tissue. Currently, these compounds are prepared on resin through a unidirectional solid-phase synthesis. To extend the utility of these compounds for therapeutic and research applications, a scalable solution-phase synthesis of Arg(8) (1) has been developed on the basis of a segment doubling strategy that proceeds in 13 steps and 28% overall yield from 4, including a novel one-step perdeprotection-perguanidinylation reaction.

  DOI：

  10.1021/ol0161108
• 作为产物：
  描述：

  Boc-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-OH 、 H-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-OBn.HCl 在 N-甲基吗啉 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 1.0h， 以97%的产率得到Boc-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-Orn(Tfa)-OBn
  参考文献：
  名称：

  An Efficient, Scalable Synthesis of the Molecular Transporter Octaarginine via a Segment Doubling Strategy

  摘要：

  [GRAPHICS]Short oligomers of arginine function as remarkably efficient molecular transporters of drugs and probe molecules into cells and tissue. Currently, these compounds are prepared on resin through a unidirectional solid-phase synthesis. To extend the utility of these compounds for therapeutic and research applications, a scalable solution-phase synthesis of Arg(8) (1) has been developed on the basis of a segment doubling strategy that proceeds in 13 steps and 28% overall yield from 4, including a novel one-step perdeprotection-perguanidinylation reaction.

  DOI：

  10.1021/ol0161108

文献信息

• An Efficient, Scalable Synthesis of the Molecular Transporter Octaarginine via a Segment Doubling Strategy
  作者：Paul A. Wender、Theodore C. Jessop、Kanaka Pattabiraman、Erin T. Pelkey、Christopher L. VanDeusen

  DOI：10.1021/ol0161108

  日期：2001.10.1

  [GRAPHICS]Short oligomers of arginine function as remarkably efficient molecular transporters of drugs and probe molecules into cells and tissue. Currently, these compounds are prepared on resin through a unidirectional solid-phase synthesis. To extend the utility of these compounds for therapeutic and research applications, a scalable solution-phase synthesis of Arg(8) (1) has been developed on the basis of a segment doubling strategy that proceeds in 13 steps and 28% overall yield from 4, including a novel one-step perdeprotection-perguanidinylation reaction.