prop-2-enyl (2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentan-2-yl]carbamoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-1-carboxylate | 320748-85-4

• 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: prop-2-enyl (2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentan-2-yl]carbamoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-1-carboxylate
• CAS: 320748-85-4
• 化学式: C₄₇H₇₃N₅O₉Si₂
• 分子量: 908.296
• InChiKey: RXJMHBCWOQWRTB-FFDWOFMBSA-N

物化性质

• 密度：
  1.13±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  9.52
• 重原子数：
  63
• 可旋转键数：
  23
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  171
• 氢给体数：
  2
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  prop-2-enyl (2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentan-2-yl]carbamoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-1-carboxylate 在 四(三苯基膦)钯 三正丁基氢锡 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 benzyl N-[(4S)-4-[[(2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-2,3,3a,4,5,6,7,7a-octahydro-1H-indole-2-carbonyl]amino]-5-[tert-butyl(dimethyl)silyl]oxypentyl]-N-[(E)-N'-phenylmethoxycarbonylcarbamimidoyl]carbamate
  参考文献：
  名称：

  Total Synthesis and Stereochemical Revision of (+)-Aeruginosin 298-A

  摘要：

  [GRAPHICS]Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of L-tyrosine. Synthesis of the proposed sequence of (+)-aeruginosin 298-A did not provide the natural product. Incorporation of a D-leucine residue, in contrast, led to the total synthesis of this thrombin inhibitor.

  DOI：

  10.1021/ol006759x
• 作为产物：
  描述：

  L-精氨酸盐酸盐 在 四(三苯基膦)钯 N-甲基吗啉 、 咪唑 、 4-二甲氨基吡啶 、 sodium hydroxide 、 iPr₂NEt₃ 、 五氟苯基二苯基磷酸酯 、 三正丁基氢锡 、 potassium carbonate 、 溶剂黄146 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 91.02h， 生成 prop-2-enyl (2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-2-[[(2S)-1-[tert-butyl(dimethyl)silyl]oxy-5-[phenylmethoxycarbonyl-(N'-phenylmethoxycarbonylcarbamimidoyl)amino]pentan-2-yl]carbamoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-1-carboxylate
  参考文献：
  名称：

  Total Synthesis and Stereochemical Revision of (+)-Aeruginosin 298-A

  摘要：

  [GRAPHICS]Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of L-tyrosine. Synthesis of the proposed sequence of (+)-aeruginosin 298-A did not provide the natural product. Incorporation of a D-leucine residue, in contrast, led to the total synthesis of this thrombin inhibitor.

  DOI：

  10.1021/ol006759x

文献信息

• Total Synthesis and Stereochemical Revision of (+)-Aeruginosin 298-A
  作者：Peter Wipf、Joey-Lee Methot

  DOI：10.1021/ol006759x

  日期：2000.12.1

  [GRAPHICS]Novel routes toward both enantiomers of the bicyclic proline surrogate 2-carboxy-6-hydroxyoctahydroindole, i.e., Choi, were developed on the basis of the oxidative cyclization of L-tyrosine. Synthesis of the proposed sequence of (+)-aeruginosin 298-A did not provide the natural product. Incorporation of a D-leucine residue, in contrast, led to the total synthesis of this thrombin inhibitor.