(R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester | 320748-87-6

• 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: (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester
• 英文别名: benzyl (2R)-2-[[(2R)-2-[tert-butyl(dimethyl)silyl]oxy-3-[4-tri(propan-2-yl)silyloxyphenyl]propanoyl]amino]-4-methylpentanoate
• CAS: 320748-87-6
• 化学式: C₃₇H₆₁NO₅Si₂
• 分子量: 656.066
• InChiKey: MAMIRBNMXWDWSW-KKLWWLSJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.45
• 重原子数：
  45
• 可旋转键数：
  18
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  73.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester 在 palladium on activated charcoal 氢气 、 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 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 23.0h， 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
• 作为产物：
  描述：

  1-benzyloxy-3-(4-triisopropylsilanyloxy-phenyl)-propan-2-(R)-ol 在 palladium on activated charcoal 咪唑 、 sodium chlorite 、 sodium dihydrogenphosphate 、 diethylphosphoryl cyanide 、 2-甲基-2-丁烯 、 氢气 、 戴斯-马丁氧化剂 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 水 、 乙酸乙酯 、 叔丁醇 为溶剂， -20.0~20.0 ℃ 、303.99 kPa 条件下， 反应 65.08h， 生成 (R)-2-[(R)-2-(tert-Butyl-dimethyl-silanyloxy)-3-(4-triisopropylsilanyloxy-phenyl)-propionylamino]-4-methyl-pentanoic acid benzyl ester
  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.