(S)-Pyrrolidine-1,2-dicarboxylic acid 2-((S)-1-benzyloxycarbonyl-2-methyl-propyl) ester 1-(9H-fluoren-9-ylmethyl) ester | 810685-26-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-Pyrrolidine-1,2-dicarboxylic acid 2-((S)-1-benzyloxycarbonyl-2-methyl-propyl) ester 1-(9H-fluoren-9-ylmethyl) ester
• CAS: 810685-26-8
• 化学式: C₃₂H₃₃NO₆
• 分子量: 527.617
• InChiKey: HRLHTDAXKYSBHY-VMPREFPWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.71
• 重原子数：
  39.0
• 可旋转键数：
  8.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.34
• 拓扑面积：
  82.14
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  (S)-Pyrrolidine-1,2-dicarboxylic acid 2-((S)-1-benzyloxycarbonyl-2-methyl-propyl) ester 1-(9H-fluoren-9-ylmethyl) ester 在 palladium on activated charcoal 氢气 作用下， 以 甲醇 为溶剂， 反应 0.08h， 以82.1%的产率得到(S)-Pyrrolidine-1,2-dicarboxylic acid 2-((S)-1-carboxy-2-methyl-propyl) ester 1-(9H-fluoren-9-ylmethyl) ester
  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：

  L-α-羟基异戊酸 在 4-二甲氨基吡啶 、 对甲苯磺酸 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 24.0h， 生成 (S)-Pyrrolidine-1,2-dicarboxylic acid 2-((S)-1-benzyloxycarbonyl-2-methyl-propyl) ester 1-(9H-fluoren-9-ylmethyl) ester
  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