[(2R,3S)-3-methyl-1-[[(2R)-3-methyl-1-[(2S)-1-[[(2S)-3-methyl-1-[(2R,3S)-3-methyl-1-[[(2R)-3-methyl-1-[(2S)-1-[[(2S)-3-methyl-1-[(2R)-4-methyl-1-[[(2R)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl] (2S)-2-[[(2R)-2-hydroxypropanoyl]amino]-3-methylbutanoate | 1126975-24-3

• 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: [(2R,3S)-3-methyl-1-[[(2R)-3-methyl-1-[(2S)-1-[[(2S)-3-methyl-1-[(2R,3S)-3-methyl-1-[[(2R)-3-methyl-1-[(2S)-1-[[(2S)-3-methyl-1-[(2R)-4-methyl-1-[[(2R)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl] (2S)-2-[[(2R)-2-hydroxypropanoyl]amino]-3-methylbutanoate
• CAS: 1126975-24-3
• 化学式: C₆₁H₁₀₆N₆O₁₉
• 分子量: 1227.54
• InChiKey: SPCNPTRDKPQXMI-LNTGYJGHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  86
• 可旋转键数：
  42
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  353
• 氢给体数：
  7
• 氢受体数：
  19

反应信息

• 作为反应物：
  描述：

  [(2R,3S)-3-methyl-1-[[(2R)-3-methyl-1-[(2S)-1-[[(2S)-3-methyl-1-[(2R,3S)-3-methyl-1-[[(2R)-3-methyl-1-[(2S)-1-[[(2S)-3-methyl-1-[(2R)-4-methyl-1-[[(2R)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl] (2S)-2-[[(2R)-2-hydroxypropanoyl]amino]-3-methylbutanoate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以100%的产率得到((R)-2-((((S)-2-((((2R,3S)-2-((((S)-2-((((2R,3S)-2-((((R)-2-hydroxypropanoyl)-L-valyl)oxy)-3-methylpentanoyl)-D-valyl)oxy)propanoyl)-L-valyl)oxy)-3-methylpentanoyl)-D-valyl)oxy)propanoyl)-L-valyl)oxy)-4-methylpentanoyl)-D-valine
  参考文献：
  名称：

  Antineoplastic Agents. 571. Total Synthesis of Bacillistatin 2

  摘要：

  The first total synthesis of bacillistain 2 (2) has been achieved in 24 steps and 22.9% overall yield, providing a quite efficient route with maximal convergence. Notable features of this approach include two successful applications of the Mitsunobu reaction during respective assemblies of key intermediates 22 and 27, successful employment of 2-methyl-6-nitrobenzoic anhydride (MNBA) in the formation by lactonization of a macrocyclic (36-membered) ring, and very flexible access to structural modifications of the bacillistatin-type cyclodepsipeptides.

  DOI：

  10.1021/np800607x
• 作为产物：
  描述：

  [(2R)-4-methyl-1-[[(2R)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl] (2S)-3-methyl-2-[[(2S)-2-[(2R)-3-methyl-2-[[(2R,3S)-3-methyl-2-[(2S)-3-methyl-2-[[(2S)-2-[(2R)-3-methyl-2-[[(2R,3S)-3-methyl-2-[(2S)-3-methyl-2-[[(2R)-2-phenylmethoxypropanoyl]amino]butanoyl]oxypentanoyl]amino]butanoyl]oxypropanoyl]amino]butanoyl]oxypentanoyl]amino]butanoyl]oxypropanoyl]amino]butanoate 在 20% Pd(OH)2/C 、 氢气 作用下， 以 甲醇 为溶剂， 以60 mg的产率得到[(2R,3S)-3-methyl-1-[[(2R)-3-methyl-1-[(2S)-1-[[(2S)-3-methyl-1-[(2R,3S)-3-methyl-1-[[(2R)-3-methyl-1-[(2S)-1-[[(2S)-3-methyl-1-[(2R)-4-methyl-1-[[(2R)-3-methyl-1-[(2-methylpropan-2-yl)oxy]-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopropan-2-yl]oxy-1-oxobutan-2-yl]amino]-1-oxopentan-2-yl] (2S)-2-[[(2R)-2-hydroxypropanoyl]amino]-3-methylbutanoate
  参考文献：
  名称：

  Antineoplastic Agents. 571. Total Synthesis of Bacillistatin 2

  摘要：

  The first total synthesis of bacillistain 2 (2) has been achieved in 24 steps and 22.9% overall yield, providing a quite efficient route with maximal convergence. Notable features of this approach include two successful applications of the Mitsunobu reaction during respective assemblies of key intermediates 22 and 27, successful employment of 2-methyl-6-nitrobenzoic anhydride (MNBA) in the formation by lactonization of a macrocyclic (36-membered) ring, and very flexible access to structural modifications of the bacillistatin-type cyclodepsipeptides.

  DOI：

  10.1021/np800607x

文献信息

• Antineoplastic Agents. 571. Total Synthesis of Bacillistatin 2
  作者：George R. Pettit、Shougang Hu、John C. Knight、Jean-Charles Chapuis

  DOI：10.1021/np800607x

  日期：2009.3.27

  The first total synthesis of bacillistain 2 (2) has been achieved in 24 steps and 22.9% overall yield, providing a quite efficient route with maximal convergence. Notable features of this approach include two successful applications of the Mitsunobu reaction during respective assemblies of key intermediates 22 and 27, successful employment of 2-methyl-6-nitrobenzoic anhydride (MNBA) in the formation by lactonization of a macrocyclic (36-membered) ring, and very flexible access to structural modifications of the bacillistatin-type cyclodepsipeptides.