5-azido-3-O-benzyl-5-deoxy-L-arabino-1,4-lactone | 1038922-18-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 5-azido-3-O-benzyl-5-deoxy-L-arabino-1,4-lactone
• 英文别名: (3R,4R,5S)-5-(azidomethyl)-3-hydroxy-4-phenylmethoxyoxolan-2-one
• CAS: 1038922-18-7
• 化学式: C₁₂H₁₃N₃O₄
• 分子量: 263.253
• InChiKey: AERPPHKIKSSZBK-AXFHLTTASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  19
• 可旋转键数：
  5
• 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：

  5-azido-3-O-benzyl-5-deoxy-L-arabino-1,4-lactone 、 三氟甲磺酸酐 在 吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 0.5h， 生成 [(3R,4S,5S)-5-(azidomethyl)-2-oxo-4-phenylmethoxyoxolan-3-yl] trifluoromethanesulfonate
  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：

  5-azido-3-O-benzyl-5-deoxy-1,2-O-isopropylidene-β-L-arabinofuranose 在 三氟乙酸 、 溴 、 barium carbonate 作用下， 以 水 、 1,4-二氧六环 为溶剂， 反应 16.5h， 以90%的产率得到5-azido-3-O-benzyl-5-deoxy-L-arabino-1,4-lactone
  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.