(2S,3S)-3-{2-[(tert-butoxy)carbonylamino]ethyl}-1-[(fluoren-9-ylmethyl)oxycarbonyl]pyrrolidine-2-carboxylic acid | 370553-18-7

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (2S,3S)-3-{2-[(tert-butoxy)carbonylamino]ethyl}-1-[(fluoren-9-ylmethyl)oxycarbonyl]pyrrolidine-2-carboxylic acid
• 英文别名: (2S,3S)-1-(9H-fluoren-9-ylmethoxycarbonyl)-3-[2-[(2-methylpropan-2-yl)oxycarbonylamino]ethyl]pyrrolidine-2-carboxylic acid
• CAS: 370553-18-7
• 化学式: C₂₇H₃₂N₂O₆
• 分子量: 480.561
• InChiKey: VLWNWRTZGPICQO-SBUREZEXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  35
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  105
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-甲基三苯基氯甲烷 、 (2S,3S)-3-{2-[(tert-butoxy)carbonylamino]ethyl}-1-[(fluoren-9-ylmethyl)oxycarbonyl]pyrrolidine-2-carboxylic acid 在 三氟乙酸 、 N,N-二异丙基乙胺 、 甲醇 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以56%的产率得到trans-3-{2-[(4-methylphenyl)diphenylmethyl]aminoethyl}-N-(9-fluorenylmethyl)-L-proline
  参考文献：
  名称：

  Strategies for the Solid-Phase Diversification of Poly-l-proline-Type II Peptide Mimic Scaffolds and Peptide Scaffolds Through Guanidinylation

  摘要：

  A strategy for the solid-phase diversification of PPII mimic scaffolds through guanidinylation is presented. The approach involves the synthesis N-Pinc-N'-alkyl thioureas as diversification reagents. Analogues of Fmoc-Orn(Mtt)-OH can be incorporated into a growing peptide chain on Wang resin. Side chain deprotection with 1% TFA/CH(2)Cl(2) followed by EDCI-mediated reaction of N-Pmc-N'-alkyl thioureas with the side chain amine affords arginine analogues with modified guanidine head groups. The scope, limitations, and incidental chemistry are discussed.

  DOI：

  10.1021/jo8012258
• 作为产物：
  描述：

  fluoren-9-ylmethyl (2S,3S)-3-{2-{(tert-butoxy)carbonylamino}ethyl}-2-(hydroxymethyl)pyrrolidinecarboxylate 在 sodium dihydrogenphosphate 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 sodium hypochlorite 、 sodium chlorite 作用下， 以 乙腈 为溶剂， 以96%的产率得到(2S,3S)-3-{2-[(tert-butoxy)carbonylamino]ethyl}-1-[(fluoren-9-ylmethyl)oxycarbonyl]pyrrolidine-2-carboxylic acid
  参考文献：
  名称：

  Synthesis of Conformationally Constrained Arginine and Ornithine Analogues Based on the 3-Substituted Pyrrolidine Framework

  摘要：

  DOI：

  10.1021/jo010242x

文献信息

• Strategies for the Solid-Phase Diversification of Poly-<scp>l</scp>-proline-Type II Peptide Mimic Scaffolds and Peptide Scaffolds Through Guanidinylation
  作者：Stevenson Flemer、Alexander Wurthmann、Ahmed Mamai、José S. Madalengoitia

  DOI：10.1021/jo8012258

  日期：2008.10.3

  A strategy for the solid-phase diversification of PPII mimic scaffolds through guanidinylation is presented. The approach involves the synthesis N-Pinc-N'-alkyl thioureas as diversification reagents. Analogues of Fmoc-Orn(Mtt)-OH can be incorporated into a growing peptide chain on Wang resin. Side chain deprotection with 1% TFA/CH(2)Cl(2) followed by EDCI-mediated reaction of N-Pmc-N'-alkyl thioureas with the side chain amine affords arginine analogues with modified guanidine head groups. The scope, limitations, and incidental chemistry are discussed.
• Synthesis of Conformationally Constrained Arginine and Ornithine Analogues Based on the 3-Substituted Pyrrolidine Framework
  作者：Ahmed Mamai、Norman E. Hughes、Alexander Wurthmann、Jose S. Madalengoitia

  DOI：10.1021/jo010242x

  日期：2001.9.1