3-methylcarbonyloxymethyl-2-oxiranylmethyl acetate | 39583-14-7

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 3-methylcarbonyloxymethyl-2-oxiranylmethyl acetate
• 英文别名: 1,4-Diacetoxy-2,3-epoxybutan；2,3-bis-acetoxymethyl-oxirane；2,3-oxiranedimethanol, diacetate；[3-(Acetyloxymethyl)oxiran-2-yl]methyl acetate
• CAS: 39583-14-7
• 化学式: C₈H₁₂O₅
• 分子量: 188.18
• InChiKey: ZCNLOFYSBLYNSY-UHFFFAOYSA-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：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  65.1
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-methylcarbonyloxymethyl-2-oxiranylmethyl acetate 在 sodium azide 、 Tris-HCl buffer 、 porcine pancreatic lipase (EC 3.1.1.3, Type II) 、 氯化铵 、 sodium chloride 作用下， 以 乙醇 、 水 为溶剂， 反应 1.0h， 生成 (2S,3R)-2-azido-3,4-di(methylcarbonyloxy)butyl 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 、 丙酮 作用下， 生成 3-methylcarbonyloxymethyl-2-oxiranylmethyl 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

文献信息

• JPH1175850A
  申请人：——

  公开号：JPH1175850A

  公开（公告）日：1999-03-23
• US5276120A
  申请人：——

  公开号：US5276120A

  公开（公告）日：1994-01-04
• US5596005A
  申请人：——

  公开号：US5596005A

  公开（公告）日：1997-01-21
• Porcine pancreatic lipase mediated regio- and stereoselective hydrolysis: chemoenzymatic synthesis of (2S,3S)-2-amino-3,4-dihydroxybutyric acid
  作者：N.W. Fadnavis、Mohd. Sharfuddin、S.Kumara Vadivel

  DOI：10.1016/s0957-4166(01)00099-4

  日期：2001.4

  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.