9H-9-fluorenylmethyl (4S)-4-(2-azido-2-oxoethyl)-5-oxo-1,3-oxazolone-3-carboxylate | 918428-65-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: 9H-9-fluorenylmethyl (4S)-4-(2-azido-2-oxoethyl)-5-oxo-1,3-oxazolone-3-carboxylate
• 英文别名: 9H-fluoren-9-ylmethyl (4S)-4-(2-azido-2-oxoethyl)-5-oxo-1,3-oxazolidine-3-carboxylate
• CAS: 918428-65-6
• 化学式: C₂₀H₁₆N₄O₅
• 分子量: 392.371
• InChiKey: KRBCBCMEPBKFGI-KRWDZBQOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.9
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  87.3
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  9H-9-fluorenylmethyl (4S)-4-(2-azido-2-oxoethyl)-5-oxo-1,3-oxazolone-3-carboxylate 在 lithium hydroxide 作用下， 以 四氢呋喃 、 甲苯 为溶剂， 反应 0.25h， 生成 Fmoc-3-[[(烯丙氧基)羰基]氨基]-L-丙氨酸
  参考文献：
  名称：

  Practical and Efficient Synthesis of Orthogonally Protected α‐2,3‐Diaminopropionic Acid (2,3‐Dap), 2,4‐Diaminobutanoic Acid (2,4‐Dab), and their N‐Methylated Derivatives

  摘要：

  DOI：

  10.1080/00397910600772827
• 作为产物：
  描述：

  (S)-3-[(9H-fluoren-9-ylmethoxy)carbonyl]-5-oxo-4-oxazolidineacetic acid 在 N-甲基吗啉 、 sodium azide 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以94%的产率得到9H-9-fluorenylmethyl (4S)-4-(2-azido-2-oxoethyl)-5-oxo-1,3-oxazolone-3-carboxylate
  参考文献：
  名称：

  Practical and Efficient Synthesis of Orthogonally Protected α‐2,3‐Diaminopropionic Acid (2,3‐Dap), 2,4‐Diaminobutanoic Acid (2,4‐Dab), and their N‐Methylated Derivatives

  摘要：

  DOI：

  10.1080/00397910600772827

文献信息

• An Efficient Conversion of the Carboxylic Group of <i>N</i>-Fmoc α-Amino Acids/Peptide Acids into <i>N</i>-Formamides Employing Isocyanates as Key Intermediates
  作者：N. S. Sudarshan、N. Narendra、H. P. Hemantha、Vommina V. Sureshbabu

  DOI：10.1021/jo701371k

  日期：2007.12.1

  [Graphics]Reaction of 96% formic acid with isocyanates derived from N-Fmoc alpha-amino acids/peptide acids catalyzed by DMAP has yielded a new class of stable formamides as crystalline solids which have been characterized by IR, H-1 NMR, C-13 NMR, and mass spectroscopy. Conversion of the side chain carboxylic acid of N-Fmoc-5-oxazolidinones of Asp/Glu into the N-formyl group also has been accomplished. The reaction is simple, mild, and high yielding.
• Synthesis of Ureido-Linked Glycosylated Amino Acids from <i>N</i> ^α-Fmoc-Asp/Glu-5-oxazolidinones and Their Application to Neoglycopeptide Synthesis
  作者：Vommina V. Sureshbabu、Rao Venkataramanarao、Shankar A. Naik、N. Narendra

  DOI：10.1080/00397910802213711

  日期：2008.10.22

  A simple route for the synthesis of ureido-linked glycosylated amino acids has been described. The key step involves the reaction of isocyanates derived from N-Fmoc-Asp/Glu-5-oxazolidinones 1 with glycosyl amines followed by hydrolysis. The resulting ureido-linked glycosylated amino acids have been incorporated into peptides. The overall procedure is simple, high-yielding, and involves fewer steps.
• Practical and Efficient Synthesis of Orthogonally Protected α‐2,3‐Diaminopropionic Acid (2,3‐Dap), 2,4‐Diaminobutanoic Acid (2,4‐Dab), and their N‐Methylated Derivatives
  作者：R. V. Ramana Rao、Subramanyam J. Tantry、Vommina V. Suresh Babu

  DOI：10.1080/00397910600772827

  日期：2006.9.1