(L)-Trt-Glp-F | 214344-21-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: (L)-Trt-Glp-F
• 英文别名: (2S)-5-oxo-1-tritylpyrrolidine-2-carbonyl fluoride
• CAS: 214344-21-5
• 化学式: C₂₄H₂₀FNO₂
• 分子量: 373.427
• InChiKey: OBPAWYHUSSTIEO-NRFANRHFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  37.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (L)-Trt-Glp-F 在 sodium tetrahydroborate 作用下， 以 二乙二醇二甲醚 为溶剂， 反应 0.17h， 以85%的产率得到(S)-5-Hydroxymethyl-1-trityl-pyrrolidin-2-one
  参考文献：
  名称：

  Preparation and Properties of Enantiomerically Pure Nalpha-Tritylamino Acid Fluorides.

  摘要：

  Cyanuric fluoride-mediated fluorination of chiral N-alpha-tritylamino acids leads to the corresponding acyl fluorides which are powerful acylating agents for peptide synthesis. The acyl fluorides react with NaBH4, the stabilized phosphorane Ph3P=C(Me)CO2Me and Ruppert's reagent providing access to enantiomerically pure tritylamino alcohols, alkenes and trifluoromethyl ketones, respectively.

  DOI：

  10.3891/acta.chem.scand.52-1144
• 作为产物：
  描述：

  (L)-Trt-Glp-OH 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 反应 0.75h， 以55%的产率得到(L)-Trt-Glp-F
  参考文献：
  名称：

  (S)-N-Triphenylmethylpyroglutamyl Fluoride

  摘要：

  The title compound, C24H20FNO2, is the product of the reaction of (S)-N-triphenylmethylpyroglutamic acid with cyanuric fluoride in the presence of pyridine. The crystal structure determination shows the presence of two crystallographically independent molecules, with the two pyrrolidinyl rings adopting slightly different conformations.

  DOI：

  10.1107/s010827019800729x

文献信息

• Preparation and Properties of Enantiomerically Pure Nalpha-Tritylamino Acid Fluorides.
  作者：Georgios Karygiannis、Costas Athanassopoulos、Petros Mamos、Nikolaos Karamanos、Dionissios Papaioannou、George W. Francis、Teófilo Rojo

  DOI：10.3891/acta.chem.scand.52-1144

  日期：——

  Cyanuric fluoride-mediated fluorination of chiral N-alpha-tritylamino acids leads to the corresponding acyl fluorides which are powerful acylating agents for peptide synthesis. The acyl fluorides react with NaBH4, the stabilized phosphorane Ph3P=C(Me)CO2Me and Ruppert's reagent providing access to enantiomerically pure tritylamino alcohols, alkenes and trifluoromethyl ketones, respectively.
• (<i>S</i>)-<i>N</i>-Triphenylmethylpyroglutamyl Fluoride
  作者：V. Nastopoulos、G. Karigiannis、P. Mamos、D. Papaioannou、C. Kavounis

  DOI：10.1107/s010827019800729x

  日期：1998.11.15

  The title compound, C24H20FNO2, is the product of the reaction of (S)-N-triphenylmethylpyroglutamic acid with cyanuric fluoride in the presence of pyridine. The crystal structure determination shows the presence of two crystallographically independent molecules, with the two pyrrolidinyl rings adopting slightly different conformations.