(2R,5S)-2-(methoxycarbonyl)-5-carboxy-3,4-(isopropylidenedioxy)tetrahydrofuran | 135144-89-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (2R,5S)-2-(methoxycarbonyl)-5-carboxy-3,4-(isopropylidenedioxy)tetrahydrofuran
• 英文别名: (3aR,4R,6S,6aS)-4-methoxycarbonyl-2,2-dimethyl-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxole-6-carboxylic acid
• CAS: 135144-89-7
• 化学式: C₁₀H₁₄O₇
• 分子量: 246.217
• InChiKey: DXNMPYMJBIUZNE-BNHYGAARSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.2
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  91.3
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (2R,5S)-2-(methoxycarbonyl)-5-carboxy-3,4-(isopropylidenedioxy)tetrahydrofuran 在 lithium hydroxide 、 锂硼氢 、 水 作用下， 生成 (2S,5S)-2-carboxy-5-(hydroxymethyl)-3,4-(isopropylidenedioxy)tetrahydrofuran
  参考文献：
  名称：

  Enzymes in organic synthesis. 48. Pig liver esterase and porcine pancreatic lipase catalyzed hydrolyses of 3,4-(isopropylidenedioxy)-2,5-tetrahydrofuranyl diesters

  摘要：

  Pig liver esterase (PLE) and porcine pancreatic lipase (PPL) catalyzed hydrolyses of 2,5-bis(methoxycarbonyl) and 2,5-bis(acetoxymethyl) meso-diester derivatives of 3,4-(isopropylidenedioxy) tetrahydrofuran proceed with enantiotopic selectivity to give monoester products of up to 72% ee. Transesterification of the 2,5-bis(hydroxymethyl) derivative with trifluorethyl laurate promoted by PPL in ether also proceeds stereoselectively but in the opposite stereochemical sense from the hydrolysis of the corresponding diacetate. The data provide further examples of heteroatom and ester moiety induced reversals of stereoselectivity for the two enzymes.

  DOI：

  10.1021/jo00018a033
• 作为产物：
  描述：

  2,5-bis(methoxycarbonyl)-3,4-(isopropylidenedioxy)tetrahydrofuran 在 pig liver esterase 、 水 作用下， 反应 0.83h， 生成 (2S,5R)-2-(methoxycarbonyl)-5-carboxy-3,4-(isopropylidenedioxy)tetrahydrofuran 、 (2R,5S)-2-(methoxycarbonyl)-5-carboxy-3,4-(isopropylidenedioxy)tetrahydrofuran
  参考文献：
  名称：

  Enzymes in organic synthesis. 48. Pig liver esterase and porcine pancreatic lipase catalyzed hydrolyses of 3,4-(isopropylidenedioxy)-2,5-tetrahydrofuranyl diesters

  摘要：

  Pig liver esterase (PLE) and porcine pancreatic lipase (PPL) catalyzed hydrolyses of 2,5-bis(methoxycarbonyl) and 2,5-bis(acetoxymethyl) meso-diester derivatives of 3,4-(isopropylidenedioxy) tetrahydrofuran proceed with enantiotopic selectivity to give monoester products of up to 72% ee. Transesterification of the 2,5-bis(hydroxymethyl) derivative with trifluorethyl laurate promoted by PPL in ether also proceeds stereoselectively but in the opposite stereochemical sense from the hydrolysis of the corresponding diacetate. The data provide further examples of heteroatom and ester moiety induced reversals of stereoselectivity for the two enzymes.

  DOI：

  10.1021/jo00018a033

文献信息

• Enzymes in organic synthesis. 48. Pig liver esterase and porcine pancreatic lipase catalyzed hydrolyses of 3,4-(isopropylidenedioxy)-2,5-tetrahydrofuranyl diesters
  作者：Philip G. Hultin、Franz Josef Mueseler、J. Bryan Jones

  DOI：10.1021/jo00018a033

  日期：1991.8

  Pig liver esterase (PLE) and porcine pancreatic lipase (PPL) catalyzed hydrolyses of 2,5-bis(methoxycarbonyl) and 2,5-bis(acetoxymethyl) meso-diester derivatives of 3,4-(isopropylidenedioxy) tetrahydrofuran proceed with enantiotopic selectivity to give monoester products of up to 72% ee. Transesterification of the 2,5-bis(hydroxymethyl) derivative with trifluorethyl laurate promoted by PPL in ether also proceeds stereoselectively but in the opposite stereochemical sense from the hydrolysis of the corresponding diacetate. The data provide further examples of heteroatom and ester moiety induced reversals of stereoselectivity for the two enzymes.