4-<2-(1-benzyloxycarbonylamino-2-methylpropyl)>-5-methyl-trans-oxazoline carboxylic acid | 220717-55-5

• 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: 4-<2-(1-benzyloxycarbonylamino-2-methylpropyl)>-5-methyl-trans-oxazoline carboxylic acid
• 英文别名: (4S,5R)-5-methyl-2-[(1S)-2-methyl-1-(phenylmethoxycarbonylamino)propyl]-4,5-dihydro-1,3-oxazole-4-carboxylic acid
• CAS: 220717-55-5
• 化学式: C₁₇H₂₂N₂O₅
• 分子量: 334.372
• InChiKey: VSSQIHDJKLYTAJ-XBFCOCLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  97.2
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-<2-(1-benzyloxycarbonylamino-2-methylpropyl)>-5-methyl-trans-oxazoline carboxylic acid 在 钯 lithium hydroxide 、 氢气 、 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 乙醇 、 三乙胺 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， -10.0 ℃ 、689.47 kPa 条件下， 反应 24.33h， 生成 bistratamide D
  参考文献：
  名称：

  Total Synthesis of Bistratamide D

  摘要：

  The total synthesis of the macrocyclic hexapeptide bistratamide D is reported. The synthetic strategy involved assembly of enantiomerically pure oxazole, thiazole, and oxazoline segments derived from amino acids. Macrocyclization of the hexapeptidic aminooxazoline-oxazole-thiazole carboxylic acid fragment was accomplished by activation with O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU).

  DOI：

  10.1021/jo981664i
• 作为产物：
  描述：

  2-(1-benzyloxycarbonylamino-2-methylpropyl)-4-carbomethoxy-5-methyl-trans-oxazoline 在 sodium hydroxide 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以94%的产率得到4-<2-(1-benzyloxycarbonylamino-2-methylpropyl)>-5-methyl-trans-oxazoline carboxylic acid
  参考文献：
  名称：

  Total Synthesis of Bistratamide D

  摘要：

  The total synthesis of the macrocyclic hexapeptide bistratamide D is reported. The synthetic strategy involved assembly of enantiomerically pure oxazole, thiazole, and oxazoline segments derived from amino acids. Macrocyclization of the hexapeptidic aminooxazoline-oxazole-thiazole carboxylic acid fragment was accomplished by activation with O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU).

  DOI：

  10.1021/jo981664i

文献信息

• Syntheses and Structures of Imidazole Analogues of Lissoclinum Cyclopeptides
  作者：Gebhard Haberhauer、Frank Rominger

  DOI：10.1002/ejoc.200300207

  日期：2003.8

  The syntheses of the cyclic peptides 3−7, which contain imidazole units in their backbones and resemble naturally occurring marine cyclopeptides such as westiellamide and ascidiacyclamide, are described. Structural investigations on the trimer 3 reveal a molecular triangle conformation with all lone pairs of the imidazole nitrogen atoms and the hydrogen atoms of the secondary amides directed to the

  描述了环肽 3-7 的合成，其主链中含有咪唑单元，类似于天然存在的海洋环肽，如韦斯特酰胺和 ascidiacyclamide。对三聚体 3 的结构研究揭示了分子三角形构象，所有孤对咪唑氮原子和仲酰胺的氢原子都指向大环的中心。四聚体 4 和 6 的结构显示出扭曲的分子方形构象，杂环 (4) 和 αCH 基团 (6) 分别位于矩形的角上。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003)
• Synthesis of Cyclopeptide Alkaloids by Cyclooligomerization of Dipeptidyl Oxazolines
  作者：Peter Wipf、Chris P Miller、Charsetta M Grant

  DOI：10.1016/s0040-4020(00)00767-5

  日期：2000.11

  peptidyl oxazoline strand and positions the valine side chains in either pseudoaxial or pseudoequatorial orientations. In the former case, transannular strain prevents the formation of 12-membered cyclopeptide alkaloids. Several X-ray structures illustrate the conformational preferences in this family of marine natural product analogs.

  用Burgess试剂对Cbz-戊基苏氨酸甲酯进行环脱水，可提供顺式和反式-恶唑啉链段用于环寡聚反应。在该方法中获得的12、18、24和24个大环大环的比率是动力学控制的，并且取决于骨架α-碳的相对立体化学。分叉的氢键网络可固定肽基恶唑啉链，并将缬氨酸侧链置于假轴或假赤道方向。在前一种情况下，跨环应变阻止了12元环肽生物碱的形成。几种X射线结构说明了该海洋天然产物类似物家族的构象偏爱。
• Total Synthesis of Bistratamide D
  作者：Susan V. Downing、Enrique Aguilar、A. I. Meyers

  DOI：10.1021/jo981664i

  日期：1999.2.1

  The total synthesis of the macrocyclic hexapeptide bistratamide D is reported. The synthetic strategy involved assembly of enantiomerically pure oxazole, thiazole, and oxazoline segments derived from amino acids. Macrocyclization of the hexapeptidic aminooxazoline-oxazole-thiazole carboxylic acid fragment was accomplished by activation with O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate (HATU).