methyl (S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-hydroxybutyrate | 898529-39-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: methyl (S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-hydroxybutyrate
• 英文别名: methyl (2S)-4-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-2-hydroxybutanoate；methyl (2S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-hydroxybutanoate
• CAS: 898529-39-0
• 化学式: C₂₀H₂₁NO₅
• 分子量: 355.39
• InChiKey: BHXHWHIEMAHDQP-SFHVURJKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  26
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  84.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  methyl (S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-hydroxybutyrate 在 sodium azide 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.0h， 生成 methyl (S)-2-(N,O-di-tert-butoxycarbonylhydroxyamino)-4-(9H-fluoren-9-ylmethoxycarbonylamino)butyrate
  参考文献：
  名称：

  Synthesis of arginine-containing hydroxamate dipeptidomimetics

  摘要：

  The syntheses of arginine-containing hydroxamates using various peptide coupling methods are described. Fmoc-Arg(NO2)-Cl prepared at low temperature did not undergo intramolecular delta-lactam formation and effectively provided desired hydroxamates (8 and 10) in good yields. Fmoc and N-nitro protecting groups can be easily removed. Therefore, this report provides a facile synthesis of arginine-containing peptidomimetic compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.190
• 作为产物：
  描述：

  (S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-hydroxybutyric acid 、 碘甲烷 在 碳酸氢钠 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 48.0h， 以95%的产率得到methyl (S)-4-(9H-fluoren-9-ylmethoxycarbonylamino)-2-hydroxybutyrate
  参考文献：
  名称：

  Synthesis of arginine-containing hydroxamate dipeptidomimetics

  摘要：

  The syntheses of arginine-containing hydroxamates using various peptide coupling methods are described. Fmoc-Arg(NO2)-Cl prepared at low temperature did not undergo intramolecular delta-lactam formation and effectively provided desired hydroxamates (8 and 10) in good yields. Fmoc and N-nitro protecting groups can be easily removed. Therefore, this report provides a facile synthesis of arginine-containing peptidomimetic compounds. (c) 2006 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2006.03.190

文献信息

• Synthesis of arginine-containing hydroxamate dipeptidomimetics
  作者：Jiwon Seo、Richard B. Silverman

  DOI：10.1016/j.tetlet.2006.03.190

  日期：2006.6

  The syntheses of arginine-containing hydroxamates using various peptide coupling methods are described. Fmoc-Arg(NO2)-Cl prepared at low temperature did not undergo intramolecular delta-lactam formation and effectively provided desired hydroxamates (8 and 10) in good yields. Fmoc and N-nitro protecting groups can be easily removed. Therefore, this report provides a facile synthesis of arginine-containing peptidomimetic compounds. (c) 2006 Elsevier Ltd. All rights reserved.