(4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one | 354816-58-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one
• CAS: 354816-58-3
• 化学式: C₃₁H₂₈NO₃PS
• 分子量: 525.608
• InChiKey: RHASTRHBKAFOBQ-LITSAYRRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.84
• 重原子数：
  37.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  46.61
• 氢给体数：
  0.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one 在 lithium hydroxide 、 双(三甲基硅烷基)氨基钾 作用下， 以 四氢呋喃 、 水 、 甲苯 为溶剂， 反应 1.25h， 生成 (2R,3S)-2-azido-3-(diphenylphosphorothioyl)-3-phenylpropanoic acid
  参考文献：
  名称：

  Catalysis with Phosphine-Containing Amino Acids in Various “Turn” Motifs

  摘要：

  We have been actively involved in the development of parallel approaches for the discovery of phosphine ligands. Our approach has been based on the incorporation of phosphine-containing amino acids into peptide sequences that are designed to have stable secondary structures. We have examined helical and turn secondary structures and have reported that alkylation of cyclopentenyl acetate with dimethylmalonate can be catalyzed in high enantiomeric excess (ee) with a beta-turn-based ligand. The importance of the peptide secondary structure was demonstrated through the synthesis of a series of peptide ligands where the nature of the turn-forming residues was probed. Additionally, other turn-forming units and a variety of different phosphine-containing amino acids have been examined for their ability to control the selectivity of the allylation reaction. This paper reports the results obtained through the examination of different turn motifs as well as different phosphine substitutions on the "best" turn sequence, Pps-Pro-D-Xxx-Pps.

  DOI：

  10.1021/jo049103g
• 作为产物：
  描述：

  (S)-4-苄基-2-唑烷酮 在 正丁基锂 、 甲基氯化镁 作用下， 以 四氢呋喃 、 正己烷 为溶剂， 反应 0.5h， 生成 (4S)-4-benzyl-3-[(3R)-3-(diphenylphosphorothioyl)-3-phenylpropanoyl]-1,3-oxazolidin-2-one
  参考文献：
  名称：

  Catalysis with Phosphine-Containing Amino Acids in Various “Turn” Motifs

  摘要：

  We have been actively involved in the development of parallel approaches for the discovery of phosphine ligands. Our approach has been based on the incorporation of phosphine-containing amino acids into peptide sequences that are designed to have stable secondary structures. We have examined helical and turn secondary structures and have reported that alkylation of cyclopentenyl acetate with dimethylmalonate can be catalyzed in high enantiomeric excess (ee) with a beta-turn-based ligand. The importance of the peptide secondary structure was demonstrated through the synthesis of a series of peptide ligands where the nature of the turn-forming residues was probed. Additionally, other turn-forming units and a variety of different phosphine-containing amino acids have been examined for their ability to control the selectivity of the allylation reaction. This paper reports the results obtained through the examination of different turn motifs as well as different phosphine substitutions on the "best" turn sequence, Pps-Pro-D-Xxx-Pps.

  DOI：

  10.1021/jo049103g

文献信息

• Kinetic Resolution in Palladium-Catalyzed Asymmetric Allylic Alkylations by a P,O Ligand System
  作者：Scott R. Gilbertson、Ping Lan

  DOI：10.1021/ol0161256

  日期：2001.7.1

  [GRAPHICS]Through the investigation of peptide-based phosphine oxazoline ligands, a simple P,O ligand system was developed. This system provides palladium complexes that are capable of a very high degree of kinetic resolution of 1,3-diphenylprop-2-enyl acetate. The isolated palladium complex was synthesized, characterized, and determined to be an effective procatalyst.