benzyl N-[(4S)-4-amino-5-[tert-butyl(dimethyl)silyl]oxypentyl]-N-(N'-phenylmethoxycarbonylcarbamimidoyl)carbamate | 320748-77-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: benzyl N-[(4S)-4-amino-5-[tert-butyl(dimethyl)silyl]oxypentyl]-N-(N'-phenylmethoxycarbonylcarbamimidoyl)carbamate
• CAS: 320748-77-4
• 化学式: C₂₈H₄₂N₄O₅Si
• 分子量: 542.751
• InChiKey: DAUKBOMNBTWFLC-DEOSSOPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.41
• 重原子数：
  38
• 可旋转键数：
  15
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.46
• 拓扑面积：
  130
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  benzyl N-[(4S)-4-amino-5-[tert-butyl(dimethyl)silyl]oxypentyl]-N-(N'-phenylmethoxycarbonylcarbamimidoyl)carbamate 在 四(三苯基膦)钯 iPr₂NEt₃ 、 五氟苯基二苯基磷酸酯 、 三正丁基氢锡 、 溶剂黄146 作用下， 以 二氯甲烷 为溶剂， 反应 48.5h， 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 、 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 43.02h， 生成 benzyl N-[(4S)-4-amino-5-[tert-butyl(dimethyl)silyl]oxypentyl]-N-(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.