(S)-3-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-7-azidoheptanoic acid | 1417532-28-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 芴
• 英文名称: (S)-3-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-7-azidoheptanoic acid
• 英文别名: Fmoc-L-β³-Lys(N₃)-OH；(3S)-7-azido-3-(9H-fluoren-9-ylmethoxycarbonylamino)heptanoic acid
• CAS: 1417532-28-5
• 化学式: C₂₂H₂₄N₄O₄
• 分子量: 408.457
• InChiKey: RXNKCCDUHTYGOQ-HNNXBMFYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  90
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (S)-3-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-7-azidoheptanoic acid 、 L-缬氨酸甲酯盐酸盐 在 1-羟基苯并三唑 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 24.0h， 以99%的产率得到(S)-methyl 2-{(S)-3-[(((9H-fluoren-9-yl)methoxy)carbonyl)amino]-7-azidoheptanamido}-3-methylbutanoate
  参考文献：
  名称：

  Azide- and Alkyne-Functionalised α- and β3-Amino Acids

  摘要：

  The synthesis and full characterisation of bifunctional beta(3)-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing beta(3)-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding alpha-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis.

  DOI：

  10.1055/s-0032-1317445
• 作为产物：
  描述：

  (2S)-N-Fmoc-6-叠氮基己酸 在 N-甲基吗啉 、 silver trifluoroacetate 、 氯甲酸异丁酯 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.5h， 生成 (S)-3-{[((9H-fluoren-9-yl)methoxy)carbonyl]amino}-7-azidoheptanoic acid
  参考文献：
  名称：

  Azide- and Alkyne-Functionalised α- and β3-Amino Acids

  摘要：

  The synthesis and full characterisation of bifunctional beta(3)-amino acids that have side chains functionalised with terminal azides (S)-4 and (R)-4 or acetylenes 5 and 6 is reported for the first time. The building blocks incorporate a turn-inducing beta(3)-segment and a side chain that can be functionalised further, for example, through copper-catalysed Huisgen cycloaddition. Moreover, the corresponding alpha-amino acids 1 and 3 have been synthesised and characterised. All amino acid building blocks were of high optical purity as demonstrated by derivatisation and subsequent NMR analysis.

  DOI：

  10.1055/s-0032-1317445