(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester | 203053-79-6

• 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: (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester
• 英文别名: Cbz-Leu-Ala-Pro-OEtTMS；2-trimethylsilylethyl (2S)-1-[(2S)-2-[[(2S)-4-methyl-2-(phenylmethoxycarbonylamino)pentanoyl]amino]propanoyl]pyrrolidine-2-carboxylate
• CAS: 203053-79-6
• 化学式: C₂₇H₄₃N₃O₆Si
• 分子量: 533.74
• InChiKey: TYGPSKFWCDTTRU-PMVMPFDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  37
• 可旋转键数：
  14
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  114
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester 在 四丁基氟化铵 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 40.0h， 生成 (S)-1-[(1S,2R,3S,4R)-3-({(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carbonyl}-amino)-bicyclo[2.2.1]hept-5-ene-2-carbonyl]-pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Peptides and Pseudopeptides Incorporating an endo-(2S,3R)-Norborn-5-ene Residue as a Turn Inducer

  摘要：

  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.

  DOI：

  10.1021/jo9717651
• 作为产物：
  描述：

  (2S)-2-[[(2S)-4-甲基-2-(苯基甲氧羰基氨基)戊酰]氨基]丙酸 、 H-Pro-OTmse 在 1-羟基苯并三唑 、 N,N'-二环己基碳二亚胺 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 以70%的产率得到(S)-1-[(S)-2-((S)-2-Benzyloxycarbonylamino-4-methyl-pentanoylamino)-propionyl]-pyrrolidine-2-carboxylic acid 2-trimethylsilanyl-ethyl ester
  参考文献：
  名称：

  Synthesis of Peptides and Pseudopeptides Incorporating an endo-(2S,3R)-Norborn-5-ene Residue as a Turn Inducer

  摘要：

  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.

  DOI：

  10.1021/jo9717651

文献信息

• 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.