methyl 3-phenyl-(3S,2R)-oxy-glycyl-L-proline-L-leucinate | 330636-92-5

• 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: methyl 3-phenyl-(3S,2R)-oxy-glycyl-L-proline-L-leucinate
• 英文别名: methyl (2S)-4-methyl-2-[[(2S)-1-[(2R,3S)-3-phenyloxirane-2-carbonyl]pyrrolidine-2-carbonyl]amino]pentanoate
• CAS: 330636-92-5
• 化学式: C₂₁H₂₈N₂O₅
• 分子量: 388.464
• InChiKey: GVNNGBJWJZBOKO-XLAORIBOSA-N

物化性质

• 沸点：
  597.8±50.0 °C(Predicted)
• 密度：
  1.218±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  88.2
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl 3-phenyl-(3S,2R)-oxy-glycyl-L-proline-L-leucinate 在 lithium hydroxide 、 水 、 三乙胺 作用下， 以 甲醇 、 二甲基亚砜 为溶剂， 反应 3.01h， 生成 prop-2-enyl (2S,3S)-3-methyl-2-[[(2S)-4-methyl-2-[[(2S)-1-[(2R,3S)-3-phenyloxirane-2-carbonyl]pyrrolidine-2-carbonyl]amino]pentanoyl]amino]pentanoate
  参考文献：
  名称：

  Reverse Turn Induced π-Facial Selectivity during Polyaniline-Supported Cobalt(II) Salen Catalyzed Aerobic Epoxidation of N-Cinnamoyl l-Proline Derived Peptides

  摘要：

  A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzed by polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derived peptides 1 show a high pi-facial selectivity during these epoxidations. The origin of this diastereo-selectivity in 1 has been attributed to (i) the propensity of the N-cinnamoyl proline amide to exist predominantly as trans rotamer in CDCl3, DMSO-d(6), and CH3CN medium and (ii) existence of these peptides as organized structures (gamma- and beta-turns) due to the presence of intramolecular hydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates that the origin of the high pi-facial selectivity is due to the well-defined gamma- and beta-turns which result in the hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidation reaction.

  DOI：

  10.1021/jo020352j
• 作为产物：
  描述：

  在 polyaniline supported cobalt(II) salen 氧气 、 sodium acetate 、 三乙胺 、 异丁醛 作用下， 以 四氢呋喃 、 二甲基亚砜 、 乙腈 为溶剂， 反应 18.0h， 生成 methyl 3-phenyl-(3S,2R)-oxy-glycyl-L-proline-L-leucinate
  参考文献：
  名称：

  Reverse Turn Induced π-Facial Selectivity during Polyaniline-Supported Cobalt(II) Salen Catalyzed Aerobic Epoxidation of N-Cinnamoyl l-Proline Derived Peptides

  摘要：

  A novel chemo- and diastereoselective aerobic epoxidation of the N-cinnamoyl peptides catalyzed by polyaniline-supported cobalt(II) salen (PASCOS) is described. The N-cinnamoyl proline derived peptides 1 show a high pi-facial selectivity during these epoxidations. The origin of this diastereo-selectivity in 1 has been attributed to (i) the propensity of the N-cinnamoyl proline amide to exist predominantly as trans rotamer in CDCl3, DMSO-d(6), and CH3CN medium and (ii) existence of these peptides as organized structures (gamma- and beta-turns) due to the presence of intramolecular hydrogen bonds. An extensive solution NMR and MD simulation study on 1d and 1f indicates that the origin of the high pi-facial selectivity is due to the well-defined gamma- and beta-turns which result in the hindrance of one face of the cinnamoyl double bond in the transition state of the epoxidation reaction.

  DOI：

  10.1021/jo020352j

文献信息

• π-Facial selectivity in polyaniline supported cobalt catalysed aerobic epoxidation of N-cinnamoyl proline derivatives
  作者：E.N Prabhakaran、Jyoti Prokash Nandy、Shalini Shukla、Javed Iqbal

  DOI：10.1016/s0040-4039(00)01949-3

  日期：2001.1

  Polyaniline supported cobalt salen catalyses the facially selective aerobic epoxidation (oxygen/2-methylpropanal) of N-cinnamoyl proline derived peptides. A high diastereoselectivity is observed for peptides which are able to adopt a gamma- or beta -turn due to intramolecular hydrogen bonding. (C) 2000 Elsevier Science Ltd. Ail rights reserved.
• Synthesis and conformation of proline containing tripeptides constrained with phenylalanine-like aziridine and dehydrophenylalanine residues
  作者：E.N. Prabhakaran、Jyoti Prokash Nandy、Shalini Shukla、Amit Tewari、Saibal Kumar Das、Javed Iqbal

  DOI：10.1016/s0040-4039(02)01236-4

  日期：2002.9

  Tripeptides containing proline and analogues of phenylalanine lead to the formation of beta-turn structures. The synthesis and beta-turn properties of four such compounds are discussed. (C) 2002 Elsevier Science Ltd. All rights reserved.