ethyl (1S,3R,4R,5R,6S)-3,4-dihydroxyspiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxolane]-6-carboxylate | 188885-74-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (1S,3R,4R,5R,6S)-3,4-dihydroxyspiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxolane]-6-carboxylate
• CAS: 188885-74-7
• 化学式: C₁₁H₁₆O₆
• 分子量: 244.244
• InChiKey: PPTFVHNYNPCHQM-OAHBRNHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.11
• 重原子数：
  17.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.91
• 拓扑面积：
  85.22
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  原甲酸三乙酯 、 ethyl (1S,3R,4R,5R,6S)-3,4-dihydroxyspiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxolane]-6-carboxylate 反应 6.0h， 以80%的产率得到ethyl (1'R,2'R,3'S,4'S,6'R)-8'-ethoxyspiro[1,3-dioxolane-2,5'-7,9-dioxatricyclo[4.3.0.02,4]nonane]-3'-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740)

  摘要：

  The asymmetric synthesis of(+)-2-aminobicyclo[3.1.0]hexane-2, 6-dicarboxylic acid (LY354740) 1, a potent and selective group 2 mGluR agonist, has been accomplished starting from the readily available enantiomerically pure cyclopentenone 4. Thus, cyclopropanation with ethyl(dimethylsulfuranylidene)acetate generated in situ with DBU, followed by deketalization gave rise to the dihydroxy bicyclic ketone 9. After protecting the ketone as 1,3-dioxolane and its transformation to the orthoformate 11, this was pyrolytically deoxygenated in a sealed tube to the bicyclic enone 13. The Synthesis was completed after hydrogenation, stereoselective Bucherer-Bergs reaction and hydantoin hydrolysis, yielding LY354740 (+)-1 with an e.e. greater than or equal to 98%. (C) 1997 Elsevier Science Ltd. rights reserved.

  DOI：

  10.1016/s0957-4166(97)00001-3
• 作为产物：
  描述：

  ethyl (1R,2R,3S,4S,6R)-5-oxospiro[7,9-dioxatricyclo[4.3.0.02,4]nonane-8,1'-cyclohexane]-3-carboxylate 在 对甲苯磺酸 、 三氟乙酸 作用下， 反应 5.0h， 生成 ethyl (1S,3R,4R,5R,6S)-3,4-dihydroxyspiro[bicyclo[3.1.0]hexane-2,2'-[1,3]dioxolane]-6-carboxylate
  参考文献：
  名称：

  Asymmetric synthesis of (+)-2-aminobicyclo[3.1.0]hexane-2,6-dicarboxylic acid (LY354740)

  摘要：

  The asymmetric synthesis of(+)-2-aminobicyclo[3.1.0]hexane-2, 6-dicarboxylic acid (LY354740) 1, a potent and selective group 2 mGluR agonist, has been accomplished starting from the readily available enantiomerically pure cyclopentenone 4. Thus, cyclopropanation with ethyl(dimethylsulfuranylidene)acetate generated in situ with DBU, followed by deketalization gave rise to the dihydroxy bicyclic ketone 9. After protecting the ketone as 1,3-dioxolane and its transformation to the orthoformate 11, this was pyrolytically deoxygenated in a sealed tube to the bicyclic enone 13. The Synthesis was completed after hydrogenation, stereoselective Bucherer-Bergs reaction and hydantoin hydrolysis, yielding LY354740 (+)-1 with an e.e. greater than or equal to 98%. (C) 1997 Elsevier Science Ltd. rights reserved.

  DOI：

  10.1016/s0957-4166(97)00001-3