N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid δ-allyl ester | 144156-13-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid δ-allyl ester
• 英文别名: N²-(tert-Butoxycarbonyl)-N³-[(9-fluorenylmethoxy)carbonyl]-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid δ-allyl ester；(2S)-3-[9H-fluoren-9-ylmethoxycarbonyl-(2-oxo-2-prop-2-enoxyethyl)amino]-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
• CAS: 144156-13-8
• 化学式: C₂₈H₃₂N₂O₈
• 分子量: 524.571
• InChiKey: RXQVXMNXBYAJIY-QHCPKHFHSA-N

物化性质

• 沸点：
  702.1±60.0 °C(Predicted)
• 密度：
  1.257±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  38
• 可旋转键数：
  14
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  132
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N-Boc-L-缬氨酸 、 N-叔丁氧羰基-N'-甲苯磺酰基-L-精氨酸 、 苯甲酰氯 、 N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid δ-allyl ester 、 alkaline earth salt of/the/ methylsulfuric acid 生成 L-Aspartic acid,N-(2-amino-2-carboxyethyl)-N-benzoylglycyl-D-valyl-L-arginylglycyl-,cyclic (51?1)-peptide, (S)-
  参考文献：
  名称：

  Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis

  摘要：

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.

  DOI：

  10.1021/jo00050a013
• 作为产物：
  描述：

  二碳酸二叔丁酯 在 jones reagent 、 碳酸氢钠 作用下， 以 四氢呋喃 、 水 、 丙酮 为溶剂， 反应 17.5h， 生成 N²-(tert-Butoxycarbonyl)-N³-((9-fluorenylmethoxy)carbonyl)-N³-(carboxymethyl)-L-2,3-diaminopropanoic acid δ-allyl ester
  参考文献：
  名称：

  Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis

  摘要：

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.

  DOI：

  10.1021/jo00050a013

文献信息

• Orthogonally protected N3-(carboxymethyl)-L-2,3-diaminopropanoic acids and O-(carboxymethyl)-L-serines for solid-phase peptide synthesis
  作者：Mark S. Stanley

  DOI：10.1021/jo00050a013

  日期：1992.11

  The syntheses of the orthogonally protected N3-(carboxymethyl)-2,3-L-diaminopropanoic acids 18, 19, and 20 and O-(carboxymethyl)-L-serines 35 and 38 are described. All of the diaminopropanoic acids were prepared via reductive amination of the known oxazolidine aldehyde 9. The carboxymethyl serines were prepared via 0-alkylation of N-CBZ-L-serine. To enable incorporation of these amino acids into cyclic peptides, protecting group schemes were designed for compatibility with either Boc or Fmoc solid-phase peptide synthesis.