N-(benzyloxycarbonyl)-(2S)-(2-(2)H)-tryptophan ethyl ester | 177753-05-8

• 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: N-(benzyloxycarbonyl)-(2S)-(2-(2)H)-tryptophan ethyl ester
• 英文别名: ethyl (2S)-2-deuterio-3-(1H-indol-3-yl)-2-(phenylmethoxycarbonylamino)propanoate
• CAS: 177753-05-8
• 化学式: C₂₁H₂₂N₂O₄
• 分子量: 367.409
• InChiKey: HBEYOADCZVIALX-MDGSFACESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  27
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  80.4
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-(benzyloxycarbonyl)-(2S)-(2-(2)H)-tryptophan ethyl ester 在 臭氧 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以33%的产率得到N'-formyl,N-(benzyloxycarbonyl)-(2S)-(2-(2)H)-kynurenine ethyl ester
  参考文献：
  名称：

  Two syntheses of 2S-[2-2H]-kynurenine

  摘要：

  The synthesis of 2S-[2-H-2]-kynurenine is described using two different routes. Diacetylation/racemisation of racemic kynurenine in deuterium oxide followed by acylase catalysed resolution is the most direct route. The alternative is to prepare 2S-[2-H-2]-tryptophan by a similar procedure and then convert this through to 2S-[2-H-2]-kynurenine via ozonolysis. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/0960-894x(96)00128-x
• 作为产物：
  描述：

  DL-色氨酸 在 氯化亚砜 、 氘氧化钠 、 氨 、 重水 、 sodium carbonate 作用下， 以 水 为溶剂， 反应 1.0h， 生成 N-(benzyloxycarbonyl)-(2S)-(2-(2)H)-tryptophan ethyl ester
  参考文献：
  名称：

  Synthesis of 2S-[2-2H]-kynurenine and use in kinetic isotope effect studies with kynureninase

  摘要：

  2S-[2-H-2]-Kynurenine has been synthesised by two different routes. Diacetylation/racemisation of racemic kynurenine in deuterium oxide followed by acylase catalysed resolution provides the most direct method, The alternative is to prepare 2S-[2-H-2]-tryptophan by a similar procedure and then convert this through to 2S-[2-H-2]-kynurenine via ozonolysis. Preliminary results on measurements of the primary deuterium isotope effect, and solvent isotope effect, are described. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4020(97)10013-8

文献信息

• Synthesis of 2S-[2-2H]-kynurenine and use in kinetic isotope effect studies with kynureninase
  作者：Fiona C Ross、Nigel P Botting、Paul D Leeson

  DOI：10.1016/s0040-4020(97)10013-8

  日期：1997.11

  2S-[2-H-2]-Kynurenine has been synthesised by two different routes. Diacetylation/racemisation of racemic kynurenine in deuterium oxide followed by acylase catalysed resolution provides the most direct method, The alternative is to prepare 2S-[2-H-2]-tryptophan by a similar procedure and then convert this through to 2S-[2-H-2]-kynurenine via ozonolysis. Preliminary results on measurements of the primary deuterium isotope effect, and solvent isotope effect, are described. (C) 1997 Elsevier Science Ltd.
• Two syntheses of 2S-[2-2H]-kynurenine
  作者：Fiona C. Ross、Nigel P. Botting、Paul D. Leeson

  DOI：10.1016/0960-894x(96)00128-x

  日期：1996.4

  The synthesis of 2S-[2-H-2]-kynurenine is described using two different routes. Diacetylation/racemisation of racemic kynurenine in deuterium oxide followed by acylase catalysed resolution is the most direct route. The alternative is to prepare 2S-[2-H-2]-tryptophan by a similar procedure and then convert this through to 2S-[2-H-2]-kynurenine via ozonolysis. Copyright (C) 1996 Elsevier Science Ltd