(2S,3S,4S)-4-(azidomethyl)-3-phenylmethoxyoxetane-2-carboxylic acid | 1038922-20-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: (2S,3S,4S)-4-(azidomethyl)-3-phenylmethoxyoxetane-2-carboxylic acid
• CAS: 1038922-20-1
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: JVMRIYFMUKQJME-DCAQKATOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.9
• 重原子数：
  19
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  70.1
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2S,3S,4S)-4-(azidomethyl)-3-phenylmethoxyoxetane-2-carboxylic acid 、 isopropyl (2S,3S,4S)-4-(aminomethyl)-3-(benzyloxy)oxetane-2-carboxylate 在 O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 16.0h， 以89%的产率得到isopropyl 2,4-anhydro-5-(2,4-anhydro-5-azido-3-O-benzyl-5-deoxy-L-ribononamido)-3-O-benzyl-5-deoxy-L-ribonate
  参考文献：
  名称：

  Oxetane amino acids: synthesis of tetrameric and hexameric carbopeptoids derived from l-ribo 4-(aminomethyl)-oxetan-2-carboxylic acid

  摘要：

  The synthesis of methyl 2,4-anhydro-5-azido-3-O-benzyl-5-deoxy-L-ribonate, a delta-2,4-cis-oxetane-azido ester scaffold derived from L-arabinose, is reported. Iterative coupling methods were utilised to form homo-oligomers up to the hexamer in order to investigate the secondary structural preferences of these systems. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.030
• 作为产物：
  描述：

  methyl 2,4-anhydro-5-azido-3-O-benzyl-5-deoxy-L-ribonate 在 sodium hydroxide 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 6.0h， 生成 (2S,3S,4S)-4-(azidomethyl)-3-phenylmethoxyoxetane-2-carboxylic acid
  参考文献：
  名称：

  Oxetane amino acids: synthesis of tetrameric and hexameric carbopeptoids derived from l-ribo 4-(aminomethyl)-oxetan-2-carboxylic acid

  摘要：

  The synthesis of methyl 2,4-anhydro-5-azido-3-O-benzyl-5-deoxy-L-ribonate, a delta-2,4-cis-oxetane-azido ester scaffold derived from L-arabinose, is reported. Iterative coupling methods were utilised to form homo-oligomers up to the hexamer in order to investigate the secondary structural preferences of these systems. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2008.03.030

文献信息

• Oxetane amino acids: synthesis of tetrameric and hexameric carbopeptoids derived from l-ribo 4-(aminomethyl)-oxetan-2-carboxylic acid
  作者：Beatrice Lopez-Ortega、Sarah F. Jenkinson、Timothy D.W. Claridge、George W.J. Fleet

  DOI：10.1016/j.tetasy.2008.03.030

  日期：2008.5

  The synthesis of methyl 2,4-anhydro-5-azido-3-O-benzyl-5-deoxy-L-ribonate, a delta-2,4-cis-oxetane-azido ester scaffold derived from L-arabinose, is reported. Iterative coupling methods were utilised to form homo-oligomers up to the hexamer in order to investigate the secondary structural preferences of these systems. (C) 2008 Elsevier Ltd. All rights reserved.