Z-D-Leu-Gly-OMe | 62188-57-2

• 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: Z-D-Leu-Gly-OMe
• 英文别名: Methyl ((benzyloxy)carbonyl)-D-leucylglycinate；methyl 2-[[(2R)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]acetate
• CAS: 62188-57-2
• 化学式: C₁₇H₂₄N₂O₅
• 分子量: 336.388
• InChiKey: XJNLCCIXRQPNFH-CQSZACIVSA-N

物化性质

• 熔点：
  88-89 °C
• 沸点：
  516.4±40.0 °C(Predicted)
• 密度：
  1.146±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  24
• 可旋转键数：
  10
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  93.7
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  N-苄氧羰基-DL-亮氨酸 、 甘胺酸甲酯 在 N-甲基吗啉 、 DMT*brucine tetrafluoroborate 、 马钱子碱 作用下， 以 乙腈 为溶剂， 以91%的产率得到Z-D-Leu-Gly-OMe
  参考文献：
  名称：

  Design, Synthesis, and Application of Enantioselective Coupling Reagent with a Traceless Chiral Auxiliary

  摘要：

  Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure of a chiral auxiliary after the activation of the carboxylic function, all of the subsequent stages of the coupling reaction proceed without any perturbation caused by a chirality discriminator (traceless). Therefore, the advantageous coupling conditions, configuration, and enantiomeric purity of the final product are entirely predictable from the model experiment.

  DOI：

  10.1021/ol802691x

文献信息

• PEPTIDE AMIDE COMPOUND AND PREPARATION METHOD AND MEDICAL USE THEREOF
  申请人：Sichuan Haisco Pharmaceutical Co., Ltd.

  公开号：EP3656782B1

  公开（公告）日：2021-12-22
• Design, Synthesis, and Application of Enantioselective Coupling Reagent with a Traceless Chiral Auxiliary
  作者：Beata Kolesinska、Zbigniew J. Kaminski

  DOI：10.1021/ol802691x

  日期：2009.2.5

  Stable chiral N-triazinylbrucinium tetrafluoroborate enantioselectively activates racemic carboxylic acids yielding enantiomerically enriched amides, esters, and dipeptides with er from 8:92 to 0.5:99.5. Due to the departure of a chiral auxiliary after the activation of the carboxylic function, all of the subsequent stages of the coupling reaction proceed without any perturbation caused by a chirality discriminator (traceless). Therefore, the advantageous coupling conditions, configuration, and enantiomeric purity of the final product are entirely predictable from the model experiment.