ethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate | 90673-92-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: ethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate
• 英文别名: Ethyl 3,8-dioxatricyclo[3.2.1.02,4]octane-6-carboxylate
• CAS: 90673-92-0
• 化学式: C₉H₁₂O₄
• 分子量: 184.192
• InChiKey: CTBFCPLDMFYQOQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  13
• 可旋转键数：
  3
• 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

• 作为产物：
  描述：

  (+/-)-ethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate 在 pig liver esterase 作用下， 反应 24.0h， 生成 ethyl 3,8-dioxatricyclo[3.2.1.0(2,4)]octane-6-carboxylate 、 2,3-epoxy-7-oxabicyclo[2.2.1]heptane-5-carboxylic acid
  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

文献信息

• PROCESS FOR THE PRODUCTION OF 5-OXY-7-OXABICYCLO- 4.1.0]HEPT-3-E NE-3-CARBOXYLIC ACID ESTERS
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP1245569A1

  公开（公告）日：2002-10-02

  The present invention provides a method of producing 5-oxy-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ester economically, industrially advantageously and efficiently in a large amount. The present invention is a method of producing 5-oxy-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ester (X), which is shown in the following scheme. wherein each symbol is as defined in the specification.

  本发明提供了一种经济、工业化和高效地大量生产5-氧-7-氧杂双环[4.1.0]庚-3-烯-3-羧酸酯的方法。本发明是一种生产 5-氧-7-氧杂双环[4.1.0]庚-3-烯-3-羧酸酯（X）的方法，其生产方案如下所示。 其中各符号如说明书中所定义。
• Endo-2,3-epoxy-7-oxabicylco[2.2.1]heptane-endo-5-carboxylic acid derivative
  申请人：SAGAMI CHEMICAL RESEARCH CENTER

  公开号：EP1486499A1

  公开（公告）日：2004-12-15

  The present invention provides a method of producing 5-oxy-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ester economically, industrially advantageously and efficiently in a large amount. The present invention is a method of producing 5-oxy-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ester (X), which is shown in the following scheme. wherein each symbol is as defined in the specification.

  本发明提供了一种经济、工业化和高效地大量生产5-氧-7-氧杂双环[4.1.0]庚-3-烯-3-羧酸酯的方法。本发明是一种生产 5-氧-7-氧杂双环[4.1.0]庚-3-烯-3-羧酸酯（X）的方法，其生产方案如下所示。 其中各符号如说明书中所定义。
• US6797832B1
  申请人：——

  公开号：US6797832B1

  公开（公告）日：2004-09-28
• 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
  作者：Manabu Hamada、Yoshikazu Inami、Yasuhito Nagai、Toshinori Higashi、Mitsuru Shoji、Seiichiro Ogawa、Kazuo Umezawa、Takeshi Sugai

  DOI：10.1016/j.tetasy.2009.07.049

  日期：2009.9

  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