methyl (2S,3aS,6R,7aS)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]-6-(2,2,2-trifluoroacetyl)oxy-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylate | 444911-13-1

• 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: methyl (2S,3aS,6R,7aS)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]-6-(2,2,2-trifluoroacetyl)oxy-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylate
• CAS: 444911-13-1
• 化学式: C₂₆H₃₃F₃N₂O₇
• 分子量: 542.552
• InChiKey: UMPGKPTWZYIUHB-WPVAHCMFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  38
• 可旋转键数：
  10
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  111
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  methyl (2S,3aS,6R,7aS)-1-[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]-6-(2,2,2-trifluoroacetyl)oxy-2,3,3a,4,5,6,7,7a-octahydroindole-2-carboxylate 在 N-甲基吗啉 、 盐酸 、 lithium hydroxide 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 71.33h， 生成
  参考文献：
  名称：

  Synthesis of Microcin SF608

  摘要：

  The first total synthesis of aquatic peptide microcin SF608 is described. Coupling of L-Hpla with the dipeptide L-Phe-L-Choi followed by coupling with agmatine and a deprotection step gave microcin SF608. In addition, the levorotatory character of L-Hpla (5) was thoroughly established, and the conformational analysis of L-Choi containing peptides 1 and 8-10 was performed using NMR spectroscopy to examine the cis-trans isomer equilibrium of the L-Phe-L-Choi amide bond.

  DOI：

  10.1021/jo025709y
• 作为产物：
  描述：

  BOC-L-苯丙氨酸 、 三氟乙酸 、 methyl (2S,3aS,6R,7aS)-1-tert-butoxycarbonyl-6-hydroxy-octahydroindole-2-carboxylate 在 N-甲基吗啉 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 作用下， 以 二氯甲烷 为溶剂， 反应 24.5h， 以225 mg的产率得到(2S,3aS,6R,7aS)-1-((S)-2-tert-Butoxycarbonylamino-3-phenyl-propionyl)-6-hydroxy-octahydro-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Synthesis of Microcin SF608

  摘要：

  The first total synthesis of aquatic peptide microcin SF608 is described. Coupling of L-Hpla with the dipeptide L-Phe-L-Choi followed by coupling with agmatine and a deprotection step gave microcin SF608. In addition, the levorotatory character of L-Hpla (5) was thoroughly established, and the conformational analysis of L-Choi containing peptides 1 and 8-10 was performed using NMR spectroscopy to examine the cis-trans isomer equilibrium of the L-Phe-L-Choi amide bond.

  DOI：

  10.1021/jo025709y

文献信息

• Synthesis of Microcin SF608
  作者：Nativitat Valls、Mercè Vallribera、Meritxell López-Canet、Josep Bonjoch

  DOI：10.1021/jo025709y

  日期：2002.7.1

  The first total synthesis of aquatic peptide microcin SF608 is described. Coupling of L-Hpla with the dipeptide L-Phe-L-Choi followed by coupling with agmatine and a deprotection step gave microcin SF608. In addition, the levorotatory character of L-Hpla (5) was thoroughly established, and the conformational analysis of L-Choi containing peptides 1 and 8-10 was performed using NMR spectroscopy to examine the cis-trans isomer equilibrium of the L-Phe-L-Choi amide bond.