(2R,3aR,6R,7aR)-6-Acetoxy-1-{(R)-2-[(S)-2-acetoxy-3-(4-benzyloxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-octahydro-indole-2-carboxylic acid methyl ester | 501368-60-1

• 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: (2R,3aR,6R,7aR)-6-Acetoxy-1-{(R)-2-[(S)-2-acetoxy-3-(4-benzyloxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-octahydro-indole-2-carboxylic acid methyl ester
• CAS: 501368-60-1
• 化学式: C₃₆H₄₆N₂O₉
• 分子量: 650.769
• InChiKey: PRQQFJNUHWCTMS-GHKDMPBJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.15
• 重原子数：
  47.0
• 可旋转键数：
  13.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  137.54
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  (2R,3aR,6R,7aR)-6-Acetoxy-1-{(R)-2-[(S)-2-acetoxy-3-(4-benzyloxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-octahydro-indole-2-carboxylic acid methyl ester 在 palladium on activated charcoal N-甲基吗啉 、 lithium hydroxide 、 氢气 、 1-羟基苯并三唑 、 1-(3-二甲基氨基丙基)-3-乙基碳二亚胺 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 62.0h， 生成 (2R,3aR,6R,7aR)-6-Hydroxy-1-{(R)-2-[(S)-2-hydroxy-3-(4-hydroxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-octahydro-indole-2-carboxylic acid amide
  参考文献：
  名称：

  Syntheses of Both the Putative and Revised Structures of Aeruginosin EI461 Bearing a New Bicyclic α-Amino Acid

  摘要：

  [GRAPHICS]The putative structure of the naturally occurring aquatic peptide aeruginosin EI461 has been prepared from D-tyrosine. A corrected structure for aeruginosin EI461 is proposed, and the structure is proven by synthesis, which was accomplished using the new alpha-amino acid (2S,-3aR,6R,7aR)-6-hydroxy-2-carboxyoctahydroindole, prepared from L-tyrosine. Succesive couplings of the dipeptide D-Leu-3a,7a-diepi-L-Choi with L-Hpla and NH4OH and a deprotection step gave aeruginosin EI461.

  DOI：

  10.1021/ol0273250
• 作为产物：
  描述：

  (2R,3aR,6R,7aR)-6-Hydroxy-octahydro-indole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester 在 N-甲基吗啉 、 4-二甲氨基吡啶 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 生成 (2R,3aR,6R,7aR)-6-Acetoxy-1-{(R)-2-[(S)-2-acetoxy-3-(4-benzyloxy-phenyl)-propionylamino]-4-methyl-pentanoyl}-octahydro-indole-2-carboxylic acid methyl ester
  参考文献：
  名称：

  Syntheses of Both the Putative and Revised Structures of Aeruginosin EI461 Bearing a New Bicyclic α-Amino Acid

  摘要：

  [GRAPHICS]The putative structure of the naturally occurring aquatic peptide aeruginosin EI461 has been prepared from D-tyrosine. A corrected structure for aeruginosin EI461 is proposed, and the structure is proven by synthesis, which was accomplished using the new alpha-amino acid (2S,-3aR,6R,7aR)-6-hydroxy-2-carboxyoctahydroindole, prepared from L-tyrosine. Succesive couplings of the dipeptide D-Leu-3a,7a-diepi-L-Choi with L-Hpla and NH4OH and a deprotection step gave aeruginosin EI461.

  DOI：

  10.1021/ol0273250