(S)-2-tert-Butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester | 70232-20-1

• 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: (S)-2-tert-Butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester
• 英文别名: (S)-benzyl 2-((tert-butoxycarbonyl)amino)-4-(dimethylamino)-4-oxobutanoate；benzyl (2S)-4-(dimethylamino)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-4-oxobutanoate
• CAS: 70232-20-1
• 化学式: C₁₈H₂₆N₂O₅
• 分子量: 350.415
• InChiKey: AFYSGIXPJFRFHB-AWEZNQCLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  25
• 可旋转键数：
  9
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  84.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (S)-2-tert-Butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester 在 palladium on activated charcoal 2,4,6-三甲基吡啶 、 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 氢气 、 三氟乙酸 、 potassium bromide 作用下， 以 二氯甲烷 、 异丙醇 为溶剂， 反应 26.0h， 生成 (S)-N¹-((S)-2-Benzylcarbamoyl-1-methyl-2-oxo-ethyl)-2-[(S)-2-(3,3-dimethyl-butyrylamino)-3,3-dimethyl-butyrylamino]-N⁴,N⁴-dimethyl-succinamide
  参考文献：
  名称：

  Short synthesis of protease inhibitors via modified Passerini condensation of N-Boc-α-aminoaldehydes

  摘要：

  Extension of the previously reported modification of Passerini multicomponent reaction (involving condensation with N-Boc-alpha-aminoaldehydes followed by a deprotection-transacylation step) to alpha-aminoacid derived carboxylic or isocyanide components, allowed the highly convergent and short synthesis of complex peptidomimetic structures, including known potent inhibitors of serine proteases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00728-1
• 作为产物：
  描述：

  Boc-L-天冬氨酸 1-苄酯 在 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 (S)-2-tert-Butoxycarbonylamino-N,N-dimethyl-succinamic acid benzyl ester
  参考文献：
  名称：

  Short synthesis of protease inhibitors via modified Passerini condensation of N-Boc-α-aminoaldehydes

  摘要：

  Extension of the previously reported modification of Passerini multicomponent reaction (involving condensation with N-Boc-alpha-aminoaldehydes followed by a deprotection-transacylation step) to alpha-aminoacid derived carboxylic or isocyanide components, allowed the highly convergent and short synthesis of complex peptidomimetic structures, including known potent inhibitors of serine proteases. (C) 2002 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(02)00728-1

文献信息

• Distal Stereocontrol Using Guanidinylated Peptides as Multifunctional Ligands: Desymmetrization of Diarylmethanes via Ullman Cross-Coupling
  作者：Byoungmoo Kim、Alex J. Chinn、Daniel R. Fandrick、Chris H. Senanayake、Robert A. Singer、Scott J. Miller

  DOI：10.1021/jacs.6b03444

  日期：2016.6.29

  guanidine-containing peptides as multifunctional ligands for transition-metal catalysis and its application in the remote desymmetrization of diarylmethanes via copper-catalyzed Ullman cross-coupling. Through design of these peptides, high levels of enantioinduction and good isolated yields were achieved in the long-range asymmetric cross-coupling (up to 93:7 er and 76% yield) between aryl bromides and malonates

  我们报道了一类新型含胍肽作为过渡金属催化多功能配体的开发及其在通过铜催化乌尔曼交叉偶联二芳基甲烷远程去对称化中的应用。通过这些肽的设计，芳基溴和丙二酸之间的长程不对称交叉偶联（高达 93:7 er 和 76% 产率）实现了高水平的对映诱导和良好的分离产率。我们的机制研究表明，远端立体控制是通过肽的路易斯碱性C端羧酸酯与底物的远端芳烃之间的Cs桥相互作用来实现的。