FMOC-D-Ala-L-PheOMe | 93710-17-9

• 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: FMOC-D-Ala-L-PheOMe
• 英文别名: methyl (2S)-2-[[(2R)-2-(9H-fluoren-9-ylmethoxycarbonylamino)propanoyl]amino]-3-phenylpropanoate
• CAS: 93710-17-9
• 化学式: C₂₈H₂₈N₂O₅
• 分子量: 472.541
• InChiKey: OBOLFWBUGDJTNK-CJAUYULYSA-N

物化性质

• 熔点：
  174-176 °C
• 沸点：
  695.0±55.0 °C(Predicted)
• 密度：
  1.228±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  35
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 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：

  芴甲氧羰基-DL-丙氨酸 、 L-苯丙氨酸甲酯盐酸盐 在 N-甲基吗啉 、 DMT*brucine tetrafluoroborate 、 马钱子碱 作用下， 以 乙腈 为溶剂， 以92%的产率得到FMOC-D-Ala-L-PheOMe
  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

• 4-Iodine <i>N</i>-Methylpyridinium-Mediated Peptide Synthesis
  作者：Wanjin Zhong、Chuan Wan、Ziyuan Zhou、Chuan Dai、Yichi Zhang、Fei Lu、Feng Yin、Zigang Li

  DOI：10.1021/acs.orglett.3c03539

  日期：2023.12.8

  Through systematic optimization of halopyridinium compounds, we established a peptide coupling protocol utilizing 4-iodine N-methylpyridinium (4IMP) for solid-phase peptide synthesis (SPPS). The 4IMP coupling reagent is easily prepared, bench stable, and cost-effective. Employing 4IMP in the SPPS process has showcased remarkable chemoselectivity and efficiency, effectively eliminating racemization

  通过对卤代吡啶化合物的系统优化，我们建立了利用 4-碘N-甲基吡啶 ( 4IMP ) 进行固相肽合成 (SPPS) 的肽偶联方案。 4IMP偶联试剂易于制备、工作台稳定且经济高效。在 SPPS 工艺中采用4IMP表现出了卓越的化学选择性和效率，有效消除了外消旋和差向异构化。通过直接利用市售的 SPPS 氨基酸底物成功合成一系列肽，证实了这一成就。
• Davies, John S.; Hakeem, Essam, Journal of the Chemical Society. Perkin transactions II, 1984, # 8, p. 1387 - 1392
  作者：Davies, John S.、Hakeem, Essam

  DOI：——

  日期：——
• The method of preparation of enantiomerically enriched products of condensation from racemic acids or acids of the low enentiomeric purity
  申请人：Politechnika Lódzka

  公开号：EP2418190B1

  公开（公告）日：2013-08-28
• 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.