methyl (1R,2S,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxybicyclo[3.3.0]octane-2-carboxylate | 204515-11-7

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: methyl (1R,2S,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxybicyclo[3.3.0]octane-2-carboxylate
• CAS: 204515-11-7
• 化学式: C₁₈H₃₂O₅Si
• 分子量: 356.535
• InChiKey: QSCNOLOOHUMQKI-XGUBFFRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  24.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  53.99
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl (1R,2S,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxybicyclo[3.3.0]octane-2-carboxylate 在 吡啶 、 lithium aluminium tetrahydride 、 四丁基氟化铵 、 二异丁基氢化铝 、 pyridinium chlorochromate 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 45.08h， 生成 (1R,2S,5S)-7,7-ethylenedioxy-2-methylbicyclo[3.3.0]octan-3-one
  参考文献：
  名称：

  Lipase-catalyzed asymmetric demethoxycarbonylation: Formal syntheses of (+)-carbacyclin, (−)-ajmalicine, and (−)-tetrahydroalstonine

  摘要：

  Both enantiomers of C-2-symmetric dimethyl 3,7-dihydroxybicyclo[3.3.0]-octa-2,6-dicarboxylate 3 were prepared in enantiomerically pure form from symmetric tetraester 1 by the lipase-catalyzed demethoxycarbonylation, respectively. Double asymmetric differentiation with lipase in the above demethoxycarbonylation was observed. Their applications to formal total syntheses of (+)-carbacyclin and (-)-ajmalicine including (-)-tetrahydroalstonine are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00616-2
• 作为产物：
  描述：

  (1S,2S,3aS,6aR)-2-Hydroxy-5-oxo-octahydro-pentalene-1-carboxylic acid 在 咪唑 、 三氟甲磺酸三甲基硅酯 作用下， 以 甲醇 、 乙醚 、 二氯甲烷 为溶剂， 反应 7.5h， 生成 methyl (1R,2S,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxybicyclo[3.3.0]octane-2-carboxylate
  参考文献：
  名称：

  Lipase-catalyzed asymmetric demethoxycarbonylation: Formal syntheses of (+)-carbacyclin, (−)-ajmalicine, and (−)-tetrahydroalstonine

  摘要：

  Both enantiomers of C-2-symmetric dimethyl 3,7-dihydroxybicyclo[3.3.0]-octa-2,6-dicarboxylate 3 were prepared in enantiomerically pure form from symmetric tetraester 1 by the lipase-catalyzed demethoxycarbonylation, respectively. Double asymmetric differentiation with lipase in the above demethoxycarbonylation was observed. Their applications to formal total syntheses of (+)-carbacyclin and (-)-ajmalicine including (-)-tetrahydroalstonine are also described. (C) 1998 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0957-4166(97)00616-2