H-Pro-OTmse | 108827-49-2

• 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: H-Pro-OTmse
• 英文别名: 2-trimethylsilylethyl (2S)-pyrrolidine-2-carboxylate
• CAS: 108827-49-2
• 化学式: C₁₀H₂₁NO₂Si
• 分子量: 215.368
• InChiKey: VOARPRYFZHGOJJ-VIFPVBQESA-N

物化性质

• 沸点：
  259.4±30.0 °C(Predicted)
• 密度：
  0.960±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.62
• 重原子数：
  14
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  38.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  H-Pro-OTmse 在 盐酸 、 benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate 、 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 N,N-二异丙基乙胺 作用下， 以 1,4-二氧六环 、 乙腈 为溶剂， 生成 (S)-1-[(S)-2-((S)-2-tert-Butoxycarbonylamino-propionylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs

  摘要：

  The incorporation of alpha-substituted beta-amino acids into a tetrapeptide motif induces a reverse turn in aprotic solvent systems as revealed by NOESY and ROESY techniques, and by CD spectra. The conformations of these compounds have been studied by molecular modeling, and further supported by performing a highly stereoselective free radical allylation reaction on an alpha-phenylselena beta-amino acid unit within the tetrapeptide. (C) 1997 Elsevier Science Ltd.

  DOI：

  10.1016/s0040-4039(97)00612-6

文献信息

• Allen, Mark C.; Brundish, Derek E.; Fullerton, Joseph D., Journal of the Chemical Society. Perkin transactions I, 1986, p. 989 - 1004
  作者：Allen, Mark C.、Brundish, Derek E.、Fullerton, Joseph D.、Wade, Roy

  DOI：——

  日期：——
• Synthesis of Peptides and Pseudopeptides Incorporating an <i>endo-</i>(2<i>S</i>,3<i>R</i>)-Norborn-5-ene Residue as a Turn Inducer
  作者：David E. Hibbs、Michael B. Hursthouse、Iwan G. Jones、Wyn Jones、K. M. Abdul Malik、Michael North

  DOI：10.1021/jo9717651

  日期：1998.3.1

  The desymmetrization of endo-norborn-5-ene-2,3-dicarboxylic anhydride (5) by proline derivatives is used to prepare peptides and pseudopeptides incorporating an endo-(2S,3R)-2-amino-3-carboxynorborn-5-ene (1) residue. The peptides contain a single conformationally constrained beta-amino acid residue, while the pseudopeptides also contain a urea linkage and two peptide chains running in parallel directions. The key step in the synthesis is a Curtius rearrangement on the amido acids 6a,b to generate an isocyanate that is then directly reacted with suitably protected amino acids and peptides to give the peptides and pseudopeptides. The synthesis of the peptide analogue 4 is also described; in this compound, the two peptide chains run parallel to one another, and the stereochemistry of the norbornene unit within compound 4 was determined by X-ray analysis of the related peptide analogue 23.
• Design of a novel secondary structure scaffolding device: Induction of a reverse turn in tetrapeptides by incorporating a β-amino acid and stereocontrolled free radical α-substitution reactions in peptide motifs
  作者：Stephen Hanessian、Hua Yang

  DOI：10.1016/s0040-4039(97)00612-6

  日期：1997.5

  The incorporation of alpha-substituted beta-amino acids into a tetrapeptide motif induces a reverse turn in aprotic solvent systems as revealed by NOESY and ROESY techniques, and by CD spectra. The conformations of these compounds have been studied by molecular modeling, and further supported by performing a highly stereoselective free radical allylation reaction on an alpha-phenylselena beta-amino acid unit within the tetrapeptide. (C) 1997 Elsevier Science Ltd.