(2S,5S)-1-[(2S,R)-methoxycarbonyl-3-phenyl-propionyl]-5-(2-hydroxyethyl)pyrrolidine-2-carboxylic acid tert-butyl ester | 208455-15-6

• 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: (2S,5S)-1-[(2S,R)-methoxycarbonyl-3-phenyl-propionyl]-5-(2-hydroxyethyl)pyrrolidine-2-carboxylic acid tert-butyl ester
• 英文别名: tert-butyl (2S,5R)-1-(2-benzyl-3-methoxy-3-oxopropanoyl)-5-(2-hydroxyethyl)pyrrolidine-2-carboxylate
• CAS: 208455-15-6
• 化学式: C₂₂H₃₁NO₆
• 分子量: 405.491
• InChiKey: NVKXUTMLTJKWOV-BLAYRMRBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  29
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  93.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,5S)-1-[(2S,R)-methoxycarbonyl-3-phenyl-propionyl]-5-(2-hydroxyethyl)pyrrolidine-2-carboxylic acid tert-butyl ester 在 4-二甲氨基吡啶 、 sodium hydride 、 三乙胺 、 sodium bromide 作用下， 以 四氢呋喃 、 二氯甲烷 、 丙酮 为溶剂， 反应 21.0h， 生成 (3R,6S,9S)-1-aza-2-oxo-3-methoxycarbonyl-3-benzyl-9-tert-butoxycarbonyl-bicyclo[4.3.0]nonane
  参考文献：
  名称：

  Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics

  摘要：

  A flexible stereoselective synthetic scheme was developed to prepare 6,5-fused bicyclic lactams, that molecular mechanics calculations revealed to have a potential as reverse-turn mimetics. The convergence of the synthetic sequence was achieved by attachment of a properly substituted malonate unit to the (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester, Stereoselective intramolecular alkylation of the malonate afforded the 6-membered lactam fused to the 2-carbalkoxy pyrrolidine nucleus. X-ray diffraction analysis of a more advanced synthetic derivative allowed the unequivocal assignment of the configuration at the newly created quaternary stereocenter as R. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00207-5
• 作为产物：
  描述：

  2-benzyl-3-methoxy-3-oxopropanoic acid 、 (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 为溶剂， 反应 12.0h， 以52%的产率得到(2S,5S)-1-[(2S,R)-methoxycarbonyl-3-phenyl-propionyl]-5-(2-hydroxyethyl)pyrrolidine-2-carboxylic acid tert-butyl ester
  参考文献：
  名称：

  Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics

  摘要：

  A flexible stereoselective synthetic scheme was developed to prepare 6,5-fused bicyclic lactams, that molecular mechanics calculations revealed to have a potential as reverse-turn mimetics. The convergence of the synthetic sequence was achieved by attachment of a properly substituted malonate unit to the (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester, Stereoselective intramolecular alkylation of the malonate afforded the 6-membered lactam fused to the 2-carbalkoxy pyrrolidine nucleus. X-ray diffraction analysis of a more advanced synthetic derivative allowed the unequivocal assignment of the configuration at the newly created quaternary stereocenter as R. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(98)00207-5

文献信息

• Stereoselective synthesis of 6,5-bicyclic reverse-turn peptidomimetics
  作者：Lino Colombo、Marcello Di Giacomo、Gloria Brusotti、Nicola Sardone、Mauro Angiolini、Laura Belvisi、Sonia Maffioli、Leonardo Manzoni、Carlo Scolastico

  DOI：10.1016/s0040-4020(98)00207-5

  日期：1998.5

  A flexible stereoselective synthetic scheme was developed to prepare 6,5-fused bicyclic lactams, that molecular mechanics calculations revealed to have a potential as reverse-turn mimetics. The convergence of the synthetic sequence was achieved by attachment of a properly substituted malonate unit to the (2S)-cis-5-(2-hydroxyethyl)proline tert-butyl ester, Stereoselective intramolecular alkylation of the malonate afforded the 6-membered lactam fused to the 2-carbalkoxy pyrrolidine nucleus. X-ray diffraction analysis of a more advanced synthetic derivative allowed the unequivocal assignment of the configuration at the newly created quaternary stereocenter as R. (C) 1998 Elsevier Science Ltd. All rights reserved.