ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methylsulfonyloxy-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methylsulfonyloxy-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate
• 化学式: C₁₃H₂₀O₇S
• 分子量: 320.364
• InChiKey: FKIQOQPXXVZXRS-GMTAPVOTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.77
• 拓扑面积：
  96.5
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  右旋奎宁酸 在 吡啶 、 磺酰氯 、 对甲苯磺酸 作用下， 以 乙醇 、 二氯甲烷 、 丙酮 为溶剂， 反应 5.0h， 生成 ethyl (3aR,7R,7aR)-2,2-dimethyl-7-methylsulfonyloxy-3a,4,7,7a-tetrahydro-1,3-benzodioxole-5-carboxylate 、 奥司他韦杂质55 、 ethyl (3aR,7R,7aR)-5-chloro-2,2-dimethyl-7-methylsulfonyloxy-4,6,7,7a-tetrahydro-3aH-1,3-benzodioxole-5-carboxylate
  参考文献：
  名称：

  METHOD FOR PREVENTING OR TREATING ARRHYTHMIA, METHOD FOR PREVENTING OR TREATING ATRIAL FIBRILLATION, MODEL OF SUSTAINED ATRIAL FIBRILLATION, METHOD FOR PRODUCING THE MODEL, AND METHOD FOR SCREENING FOR ATRIAL FIBRILLATION INHIBITOR

  摘要：

  预防或治疗心房颤动的方法，包括：向个体施用含有以下结构式（I）至（VI）中的一种化合物或其药理学可接受的盐的心房颤动抑制剂：其中在结构式（III）中，Gluc指的是葡萄糖醛酸。

  公开号：

  US20140051756A1

文献信息

• METHOD FOR PREVENTING OR TREATING ARRHYTHMIA, METHOD FOR PREVENTING OR TREATING ATRIAL FIBRILLATION, MODEL OF SUSTAINED ATRIAL FIBRILLATION, METHOD FOR PRODUCING THE MODEL, AND METHOD FOR SCREENING FOR ATRIAL FIBRILLATION INHIBITOR
  申请人：Toho University

  公开号：US20140051756A1

  公开（公告）日：2014-02-20

  A method for preventing or treating atrial fibrillation, including: administering, to an individual, an atrial fibrillation inhibitor containing a compound expressed by one of the following Structural Formulas (I) to (VI) or a pharmacologically acceptable salt thereof: where in the Structural Formula (III), Gluc refers to glucuronic acid,

  预防或治疗心房颤动的方法，包括：向个体施用含有以下结构式（I）至（VI）中的一种化合物或其药理学可接受的盐的心房颤动抑制剂：其中在结构式（III）中，Gluc指的是葡萄糖醛酸。
• Practical Total Synthesis of the Anti-Influenza Drug GS-4104
  作者：John C. Rohloff、Kenneth M. Kent、Michael J. Postich、Mark W. Becker、Harlan H. Chapman、Daphne E. Kelly、Willard Lew、Michael S. Louie、Lawrence R. McGee、Ernest J. Prisbe、Lisa M. Schultze、Richard H. Yu、Lijun Zhang

  DOI：10.1021/jo980330q

  日期：1998.6.1
• Industrial Synthesis of the Key Precursor in the Synthesis of the Anti-Influenza Drug Oseltamivir Phosphate (Ro 64-0796/002, GS-4104-02):  Ethyl (3<i>R</i>,4<i>S</i>,5<i>S</i>)-4,5-epoxy-3-(1-ethyl-propoxy)-cyclohex-1-ene-1-carboxylate
  作者：Muriel Federspiel、Rolf Fischer、Michael Hennig、Hans-Jürgen Mair、Thomas Oberhauser、Gösta Rimmler、Thomas Albiez、Jürg Bruhin、Heinrich Estermann、Carsten Gandert、Volker Göckel、Stephan Götzö、Ursula Hoffmann、Gabriel Huber、Günter Janatsch、Stephan Lauper、Odette Röckel-Stäbler、Rene Trussardi、Andreas G. Zwahlen

  DOI：10.1021/op9900176

  日期：1999.7.1

  Starting from (-)-quinic acid, the title compound was synthesized in seven chemical steps and an overall yield of 35-38%, The route of the improved Gilead synthesis was not changed, However, significant improvements in each step led to a doubled overall yield, a 30% reduction in the number of unit operations, and an excellent quality (greater than or equal to 99%) of the resulting epoxide. A highly regioselective method for the dehydration of a quinic acid to a shikimic acid derivative and for the reduction of a cyclic ketal was found, Alternatively, the title compound was synthesized in six chemical steps and 63-65% yield from commercially available (-)-shikimic acid, Compared to the optimized quinic acid route, the production time was reduced by about 50%, The quality of epoxide produced from either natural product was equivalent, Therefore (-)-shikimic acid is the preferred raw material, The absolute configuration of the epoxide was determined by X-ray single crystal structure analysis and it was demonstrated that the epoxide was stereoisomerically pure.