(Z)-2-tert-Butoxycarbonylamino-3-{3-[(Z)-2-methoxycarbonyl-2-(2-trimethylsilanyl-ethoxycarbonylamino)-vinyl]-phenyl}-acrylic acid benzyl ester | 205063-77-0

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 肉桂酸及其衍生物
• 英文名称: (Z)-2-tert-Butoxycarbonylamino-3-{3-[(Z)-2-methoxycarbonyl-2-(2-trimethylsilanyl-ethoxycarbonylamino)-vinyl]-phenyl}-acrylic acid benzyl ester
• CAS: 205063-77-0
• 化学式: C₃₁H₄₀N₂O₈Si
• 分子量: 596.753
• InChiKey: SLYKVYMVMAZKLJ-DQIQZUARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.87
• 重原子数：
  42.0
• 可旋转键数：
  11.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  129.26
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (Z)-2-tert-Butoxycarbonylamino-3-{3-[(Z)-2-methoxycarbonyl-2-(2-trimethylsilanyl-ethoxycarbonylamino)-vinyl]-phenyl}-acrylic acid benzyl ester 在 ⁺Otf^- 四丁基氟化铵 、 氢气 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 25.0 ℃ 、273.58 kPa 条件下， 反应 2.5h， 生成 (R)-3-[3-((S)-2-Amino-2-methoxycarbonyl-ethyl)-phenyl]-2-tert-butoxycarbonylamino-propionic acid benzyl ester
  参考文献：
  名称：

  Synthesis of optically active arylene bis-alanine derivatives carrying orthogonal protecting groups

  摘要：

  Derivatives of para- and meta-phenylene bis-alanine and related biphenyl systems, carrying four orthogonal protecting groups, were synthesised via combinations of Heck couplings and asymmetric hydrogenations, The intermediate unsaturated arylalanine derivatives were hydrogenated using [Rh(COD)((R,R)-DIPAMP)]+BF4- or [Rh(COD)(Me-DuPHOS)]X-+(-) as catalysts to produce the optically active, protected amino acid derivatives in greater than or equal to 98% e.e. as analysed by chiral phase HPLC. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00014-7
• 作为产物：
  描述：

  methyl 2-({[2-(trimethylsilyl)ethoxy]carbonyl}amino)acrylate 、 (E)-3-(3-Bromo-phenyl)-2-tert-butoxycarbonylamino-acrylic acid benzyl ester 在 palladium diacetate 、 四丁基氯化铵 、 碳酸氢钠 、 对苯二酚 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 18.0h， 以77%的产率得到(Z)-2-tert-Butoxycarbonylamino-3-{3-[(Z)-2-methoxycarbonyl-2-(2-trimethylsilanyl-ethoxycarbonylamino)-vinyl]-phenyl}-acrylic acid benzyl ester
  参考文献：
  名称：

  Synthesis of optically active arylene bis-alanine derivatives carrying orthogonal protecting groups

  摘要：

  Derivatives of para- and meta-phenylene bis-alanine and related biphenyl systems, carrying four orthogonal protecting groups, were synthesised via combinations of Heck couplings and asymmetric hydrogenations, The intermediate unsaturated arylalanine derivatives were hydrogenated using [Rh(COD)((R,R)-DIPAMP)]+BF4- or [Rh(COD)(Me-DuPHOS)]X-+(-) as catalysts to produce the optically active, protected amino acid derivatives in greater than or equal to 98% e.e. as analysed by chiral phase HPLC. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(98)00014-7