(-)-2-chloroethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate | 1199940-74-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧烷类
• 英文名称: (-)-2-chloroethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate
• 英文别名: 2-chloroethyl (1R,2S,4R,5S,6R)-3,8-dioxatricyclo[3.2.1.02,4]octane-6-carboxylate
• CAS: 1199940-74-3
• 化学式: C₉H₁₁ClO₄
• 分子量: 218.637
• InChiKey: QOUOIIPLVCRWPA-QQGCVABSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.3
• 重原子数：
  14
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  48.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (-)-2-chloroethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate 在 lithium hexamethyldisilazane 、 水 、 氯化铵 作用下， 以 四氢呋喃 为溶剂， 以77%的产率得到(+)-2-chloroethyl (1R,5R,6S)-5-hydroxy-7-oxabicyclo[4.1.0]hept-2-ene-3-carboxylate
  参考文献：
  名称：

  Enzyme-catalyzed resolution of 3,8-dioxatricyclo[3.2.1.02,4]octane-6-carboxylic esters and the application to the synthesis of 3-epishikimic acid

  摘要：

  3,8-Dioxatricyclo[3 2 1 0(2 4)]octane-6-carboxylic acid, whose racemic form is readily available on a large scale, is a versatile starting material for the synthesis of carbasugars and carbocyclic biologically active natural products. In this study, the enzyme-catalyzed kinetic resolution was attempted on a variety of corresponding carboxylic esters. The hydrophobic and hydrophilic properties of ester substituents greatly affected the rate of reaction and the enantioselectivity. Hydrolysis of the corresponding 2'-chlotoethyl ester with pig liver esterase worked well in a highly enantioselective manner (E = 116) to give the hydiolyzate (90.6% ee) and unreacted ester recovery (99.4% ee). The hydrolyzate is a piecursor for (-)-oseltamivir phosphate, and a route to (3S,4S,5R)-(-)-3-epishikimic acid was developed from the recovered ester. (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2009.07.049
• 作为产物：
  描述：

  (+/-)-2-chloroethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate 在 pig liver esterase 、 碳酸氢钠 作用下， 以 水 为溶剂， 以42.7%的产率得到(-)-2-chloroethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate
  参考文献：
  名称：

  Enzyme-catalyzed resolution of 3,8-dioxatricyclo[3.2.1.02,4]octane-6-carboxylic esters and the application to the synthesis of 3-epishikimic acid

  摘要：

  3,8-Dioxatricyclo[3 2 1 0(2 4)]octane-6-carboxylic acid, whose racemic form is readily available on a large scale, is a versatile starting material for the synthesis of carbasugars and carbocyclic biologically active natural products. In this study, the enzyme-catalyzed kinetic resolution was attempted on a variety of corresponding carboxylic esters. The hydrophobic and hydrophilic properties of ester substituents greatly affected the rate of reaction and the enantioselectivity. Hydrolysis of the corresponding 2'-chlotoethyl ester with pig liver esterase worked well in a highly enantioselective manner (E = 116) to give the hydiolyzate (90.6% ee) and unreacted ester recovery (99.4% ee). The hydrolyzate is a piecursor for (-)-oseltamivir phosphate, and a route to (3S,4S,5R)-(-)-3-epishikimic acid was developed from the recovered ester. (C) 2009 Elsevier Ltd All rights reserved

  DOI：

  10.1016/j.tetasy.2009.07.049