benzyl N-[(4S)-4-[[(2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-1-[(2R)-2-[[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[4-tri(propan-2-yl)silyloxyphenyl]propanoyl]amino]-4-methylpentanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]amino]-5-[tert-butyl(dimethyl)silyl]oxypentyl]-N-[(E)-N'-phenylmethoxycarbonylcarbamimidoyl]carbamate | 320748-89-8

• 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: benzyl N-[(4S)-4-[[(2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-1-[(2R)-2-[[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[4-tri(propan-2-yl)silyloxyphenyl]propanoyl]amino]-4-methylpentanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]amino]-5-[tert-butyl(dimethyl)silyl]oxypentyl]-N-[(E)-N'-phenylmethoxycarbonylcarbamimidoyl]carbamate
• CAS: 320748-89-8
• 化学式: C₇₃H₁₂₂N₆O₁₁Si₄
• 分子量: 1372.15
• InChiKey: YHHRRRKDPUYINH-HNIXLZDYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  16.44
• 重原子数：
  94
• 可旋转键数：
  35
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  210
• 氢给体数：
  3
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  benzyl N-[(4S)-4-[[(2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-1-[(2R)-2-[[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[4-tri(propan-2-yl)silyloxyphenyl]propanoyl]amino]-4-methylpentanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-2-carbonyl]amino]-5-[tert-butyl(dimethyl)silyl]oxypentyl]-N-[(E)-N'-phenylmethoxycarbonylcarbamimidoyl]carbamate 在 氢氟酸 作用下， 以 乙腈 为溶剂， 反应 2.0h， 生成
  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 、 N,N-二异丙基乙胺 、 3-(二乙氧基邻酰氧基)-1,2,3-苯并三嗪-4-酮 、 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 112.52h， 生成 benzyl N-[(4S)-4-[[(2S,3aS,6R,7aS)-6-[tert-butyl(dimethyl)silyl]oxy-1-[(2R)-2-[[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[4-tri(propan-2-yl)silyloxyphenyl]propanoyl]amino]-4-methylpentanoyl]-2,3,3a,4,5,6,7,7a-octahydroindole-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

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.