(2S,3R)-3-azido-2,4-dihydroxybutyl acetate | 354556-03-9

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2S,3R)-3-azido-2,4-dihydroxybutyl acetate
• 英文别名: [(2S,3R)-3-azido-2,4-dihydroxybutyl] acetate
• CAS: 354556-03-9
• 化学式: C₆H₁₁N₃O₄
• 分子量: 189.171
• InChiKey: WBQHGOJSKDYJEZ-PHDIDXHHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  13
• 可旋转键数：
  6
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.83
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  叔丁基二苯基氯硅烷 、 (2S,3R)-3-azido-2,4-dihydroxybutyl acetate 在 咪唑 作用下， 以89%的产率得到(2S,3R)-3-azido-2-hydroxy-4-(tert-butyldiphenyl)silyloxybutyl acetate
  参考文献：
  名称：

  Porcine pancreatic lipase mediated regio- and stereoselective hydrolysis: chemoenzymatic synthesis of (2S,3S)-2-amino-3,4-dihydroxybutyric acid

  摘要：

  Porcine pancreatic lipase was used in the chemoenzymatic hydrolysis of 2-azido-3-hydroxy-3-methylcarbonyloxybutyl acetate The reaction occurred with high regio- and stereoselectivity to give enantiomerically pure (2S.3R)-3-azido-2-4-dihydroxy butyl acetate 5 (e.e. > 99%) which was easily converted to (2S,3S)-2-amno-3.4-dihydroxybutyric acid 1. an important synthetic intermediate in the synthesis of beta -lactam antibiotics and phytosiderophores, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00099-4
• 作为产物：
  描述：

  cis-1,4-二乙酰氧基-2-丁烯 在 Oxone 、 sodium azide 、 Tris-HCl buffer 、 porcine pancreatic lipase (EC 3.1.1.3, Type II) 、 氯化铵 、 丙酮 、 sodium chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 (2S,3R)-3-azido-2,4-dihydroxybutyl acetate
  参考文献：
  名称：

  Porcine pancreatic lipase mediated regio- and stereoselective hydrolysis: chemoenzymatic synthesis of (2S,3S)-2-amino-3,4-dihydroxybutyric acid

  摘要：

  Porcine pancreatic lipase was used in the chemoenzymatic hydrolysis of 2-azido-3-hydroxy-3-methylcarbonyloxybutyl acetate The reaction occurred with high regio- and stereoselectivity to give enantiomerically pure (2S.3R)-3-azido-2-4-dihydroxy butyl acetate 5 (e.e. > 99%) which was easily converted to (2S,3S)-2-amno-3.4-dihydroxybutyric acid 1. an important synthetic intermediate in the synthesis of beta -lactam antibiotics and phytosiderophores, (C) 2001 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(01)00099-4