tert-butyl N-[(2S)-1-[5-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]pentylamino]-1-oxopropan-2-yl]carbamate | 1026696-84-3

• 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: tert-butyl N-[(2S)-1-[5-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]pentylamino]-1-oxopropan-2-yl]carbamate
• CAS: 1026696-84-3
• 化学式: C₂₁H₄₀N₄O₆
• 分子量: 444.572
• InChiKey: OHOSBZPUJWHREC-GJZGRUSLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  31
• 可旋转键数：
  14
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  tert-butyl N-[(2S)-1-[5-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]pentylamino]-1-oxopropan-2-yl]carbamate 在 1-羟基苯并三唑 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 36.0h， 生成 3-diphenylphosphanyl-N-[(2S)-1-[[(2S)-1-[5-[[(2S)-2-[[(2S)-2-[(3-diphenylphosphanylbenzoyl)amino]propanoyl]amino]propanoyl]amino]pentylamino]-1-oxopropan-2-yl]amino]-1-oxopropan-2-yl]benzamide
  参考文献：
  名称：

  “Backdoor Induction” of Chirality: Asymmetric Hydrogenation with Rhodium(I) Complexes of Triphenylphosphane-Substituted β-Turn Mimetics

  摘要：

  Bioconjugate bidentate ligands 2-10 were obtained by tethering triphenylphosphanecarboxylic acid to amino acid substituted spacers with different flexibility, ranging from a rigid enediyne-based beta-turn inducer to flexible linear aliphatic chains with up to eight carbon atoms. The 21 synthesized ligands revealed up to 81% ee selectivity in rhodium-catalyzed asymmetric hydrogenation of alpha,beta-unsaturated amino acids. The key feature of the catalysts is the prochiral coordination sphere of the catalytic metal while the chirality is transmitted by "backdoor induction" from distant hydrogen-bonded amino acids. DFT calculations were applied to study the structure and relative stability of the precatalytic organometallic Rh(I) complexes, with particular emphasis on hydrogen-bonded secondary structures.

  DOI：

  10.1021/om5005385
• 作为产物：
  描述：

  1,5-二氨基戊烷 、 BOC-ALA-HOBt 以 四氢呋喃 为溶剂， 生成 tert-butyl N-[(2S)-1-[5-[[(2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoyl]amino]pentylamino]-1-oxopropan-2-yl]carbamate
  参考文献：
  名称：

  Lyakhov; Suveyzdis; Litvinova, Pharmazie, 2000, vol. 55, # 10, p. 733 - 736

  摘要：

  DOI：

文献信息

• Lyakhov; Suveyzdis; Litvinova, Pharmazie, 2000, vol. 55, # 10, p. 733 - 736
  作者：Lyakhov、Suveyzdis、Litvinova、Andronati、Rybalko、Dyadyun

  DOI：——

  日期：——
• “Backdoor Induction” of Chirality: Asymmetric Hydrogenation with Rhodium(I) Complexes of Triphenylphosphane-Substituted β-Turn Mimetics
  作者：Zoran Kokan、Zoran Glasovac、Maja Majerić Elenkov、Matija Gredičak、Ivanka Jerić、Srećko I. Kirin

  DOI：10.1021/om5005385

  日期：2014.8.11

  Bioconjugate bidentate ligands 2-10 were obtained by tethering triphenylphosphanecarboxylic acid to amino acid substituted spacers with different flexibility, ranging from a rigid enediyne-based beta-turn inducer to flexible linear aliphatic chains with up to eight carbon atoms. The 21 synthesized ligands revealed up to 81% ee selectivity in rhodium-catalyzed asymmetric hydrogenation of alpha,beta-unsaturated amino acids. The key feature of the catalysts is the prochiral coordination sphere of the catalytic metal while the chirality is transmitted by "backdoor induction" from distant hydrogen-bonded amino acids. DFT calculations were applied to study the structure and relative stability of the precatalytic organometallic Rh(I) complexes, with particular emphasis on hydrogen-bonded secondary structures.