(2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester | 876953-56-9

• 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: (2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS: 876953-56-9
• 化学式: C₂₇H₄₁N₃O₆S
• 分子量: 535.705
• InChiKey: FCHOYVDTKDPNJP-MLNNCEHLSA-N

物化性质

• 沸点：
  718.0±60.0 °C(Predicted)
• 密度：
  1.18±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  37.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  114.04
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 、 甲酸 在 2-乙氧基-1-乙氧碳酰基-1,2-二氢喹啉 作用下， 以 氯仿 为溶剂， 反应 48.0h， 以65%的产率得到
  参考文献：
  名称：

  Chemotactic peptides: fMLF-OMe analogues incorporating proline–methionine chimeras as N-terminal residue

  摘要：

  The new fMLF analogues 1-4, incorporating chimeric S-proline-methionine residues (namely the homochiral cis-4(s)methylthio-(S)-proline (10) and the heterochiral trans-4(R)-methylthio-(S)-proline) (17) in place of the native S-methionine, have been prepared; their solution conformation and activity as agonists or antagonists of formylpeptide receptors have been studied. In addition to peptides 1-4, which maintain the Met gamma-thiomethyl-ether function, the analogues Boc-PLF-OMe (18) and For-PLF-OMe (19) devoid, as compared with 1-4, of position I side chain, have been synthesized and their activity examined. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.001
• 作为产物：
  描述：

  Boc-L-羟脯氨酸 在 N-甲基吗啉 、 吡啶 、 chromium(VI) oxide 、 sodium hydroxide 、 sodium tetrahydroborate 、 三乙胺 、 氯甲酸异丁酯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 23.5h， 生成 (2S,4R)-2-[(S)-1-((S)-1-Methoxycarbonyl-2-phenyl-ethylcarbamoyl)-3-methyl-butylcarbamoyl]-4-methylsulfanyl-pyrrolidine-1-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Chemotactic peptides: fMLF-OMe analogues incorporating proline–methionine chimeras as N-terminal residue

  摘要：

  The new fMLF analogues 1-4, incorporating chimeric S-proline-methionine residues (namely the homochiral cis-4(s)methylthio-(S)-proline (10) and the heterochiral trans-4(R)-methylthio-(S)-proline) (17) in place of the native S-methionine, have been prepared; their solution conformation and activity as agonists or antagonists of formylpeptide receptors have been studied. In addition to peptides 1-4, which maintain the Met gamma-thiomethyl-ether function, the analogues Boc-PLF-OMe (18) and For-PLF-OMe (19) devoid, as compared with 1-4, of position I side chain, have been synthesized and their activity examined. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.11.001