ditert-butyl (2S,3aS,8bS)-2-(hydroxymethyl)-8b-[3-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1H-indol-7-yl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate | 370890-27-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ditert-butyl (2S,3aS,8bS)-2-(hydroxymethyl)-8b-[3-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1H-indol-7-yl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate
• CAS: 370890-27-0
• 化学式: C₃₇H₅₀N₄O₈
• 分子量: 678.826
• InChiKey: KEVKZTNJDGTIHL-ZILLAOMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.2
• 重原子数：
  49
• 可旋转键数：
  12
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  154
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ditert-butyl (2S,3aS,8bS)-2-(hydroxymethyl)-8b-[3-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1H-indol-7-yl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate 在 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 生成 (2S,3aS,8bS)-8b-[3-[(2S)-2-carboxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]-1H-indol-7-yl]-3,4-bis[(2-methylpropan-2-yl)oxycarbonyl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2-carboxylic acid
  参考文献：
  名称：

  Total synthesis of (+)-asperazine

  摘要：

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)- asperazine (1) proposed by Crews and co- workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)- asperazine. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.05.127
• 作为产物：
  描述：

  L-色氨酸甲酯盐酸盐 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 palladium on activated charcoal N-甲基吡咯烷酮 、 盐酸 、 三乙基硅烷 、 氢氧化钾 、 sodium hydroxide 、 sodium tetrahydroborate 、 copper(l) iodide 、 三(2-呋喃基)膦 、 四甲基乙二胺 、 杀鼠酮 、 四丁基氟化铵 、 氢气 、 三甲基铝 、 仲丁基锂 、 四丁基硫酸氢铵 、 2,4-滴二甲胺盐 、 sodium hydride 、 三乙基硼氢化锂 、 sodium carbonate 、 potassium carbonate 、 对甲苯磺酸 、 二甲基亚砜 、 三氟乙酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 lithium chloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 乙醚 、 乙醇 、 二氯甲烷 、 二甲基亚砜 、 N,N-二甲基甲酰胺 、 甲苯 、 苯 为溶剂， -78.0~130.0 ℃ 、6.89 MPa 条件下， 生成 ditert-butyl (2S,3aS,8bS)-2-(hydroxymethyl)-8b-[3-[(2S)-3-hydroxy-2-[(2-methylpropan-2-yl)oxycarbonylamino]propyl]-1H-indol-7-yl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate
  参考文献：
  名称：

  Total Synthesis of Asperazine

  摘要：

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)-asperazine (1) proposed by Crews and co-workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)-asperazine.

  DOI：

  10.1021/ja016616l

文献信息

• Total synthesis of (+)-asperazine
  作者：Steven P. Govek、Larry E. Overman

  DOI：10.1016/j.tet.2007.05.127

  日期：2007.8

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)- asperazine (1) proposed by Crews and co- workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)- asperazine. (c) 2007 Elsevier Ltd. All rights reserved.
• Total Synthesis of Asperazine
  作者：Steven P. Govek、Larry E. Overman

  DOI：10.1021/ja016616l

  日期：2001.9.1

  The first total synthesis of the structurally novel cyclotryptophan alkaloid asperazine is reported. The central step in the synthetic sequence is a diastereoselective intramolecular Heck reaction in which the substituent controlling stereoselection is external to the ring being formed. This synthesis confirmed the structure of (+)-asperazine (1) proposed by Crews and co-workers and provided material for additional biological studies. The in vitro cytotoxicity originally reported for the marine isolate was not confirmed with synthetic (+)-asperazine.