tert-butyl (4E)-4-[[(3R)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1-(2-trimethylsilylethoxymethyl)indol-7-yl]-2-oxo-1-(2-trimethylsilylethoxymethyl)indol-3-yl]methylidene]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate | 370890-23-6

• 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: tert-butyl (4E)-4-[[(3R)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1-(2-trimethylsilylethoxymethyl)indol-7-yl]-2-oxo-1-(2-trimethylsilylethoxymethyl)indol-3-yl]methylidene]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
• CAS: 370890-23-6
• 化学式: C₅₀H₇₆N₄O₉Si₂
• 分子量: 933.346
• InChiKey: DOZFUOJQDIRCDC-CPHWLRBSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  10.7
• 重原子数：
  65
• 可旋转键数：
  18
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  121
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  tert-butyl (4E)-4-[[(3R)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1-(2-trimethylsilylethoxymethyl)indol-7-yl]-2-oxo-1-(2-trimethylsilylethoxymethyl)indol-3-yl]methylidene]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate 在 palladium on activated charcoal 盐酸 、 氢氧化钾 、 sodium hydroxide 、 sodium chlorite 、 sodium dihydrogenphosphate 、 2-甲基-2-丁烯 、 pyridine-SO3 complex 、 四丁基氟化铵 、 氢气 、 四丁基硫酸氢铵 、 三乙基硼氢化锂 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， -78.0~50.0 ℃ 、6.89 MPa 条件下， 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.

  DOI：

  10.1021/ja016616l
• 作为产物：
  描述：

  (R)-2,2-二甲基-3-(n-boc)-4-乙炔噁唑啉 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 四(三苯基膦)钯 1,2,2,6,6-五甲基哌啶 、 正丁基锂 、 三(2-呋喃基)膦 、 三甲基铝 、 三正丁基氢锡 、 sodium hydride 、 二甲基亚砜 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基乙酰胺 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 1.5h， 生成 tert-butyl (4E)-4-[[(3R)-3-[3-[[(4S)-2,2-dimethyl-3-[(2-methylpropan-2-yl)oxycarbonyl]-1,3-oxazolidin-4-yl]methyl]-1-(2-trimethylsilylethoxymethyl)indol-7-yl]-2-oxo-1-(2-trimethylsilylethoxymethyl)indol-3-yl]methylidene]-2,2-dimethyl-1,3-oxazolidine-3-carboxylate
  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

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.