(3S,3aR,6aS)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,3,4-tricarboxylic acid trimethyl ester | 163019-35-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (3S,3aR,6aS)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,3,4-tricarboxylic acid trimethyl ester
• 英文别名: trimethyl (3S,3aR,6aS)-2,5-dihydroxy-3,3a,6,6a-tetrahydropentalene-1,3,4-tricarboxylate
• CAS: 163019-35-0
• 化学式: C₁₄H₁₆O₈
• 分子量: 312.276
• InChiKey: YSCIQVHTSWFDJE-AYKAFODUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  22
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (3S,3aR,6aS)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,3,4-tricarboxylic acid trimethyl ester 在 吡啶 、 盐酸 、 lithium hydroxide 、 sodium triethoxyborohydride 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 为溶剂， 反应 38.5h， 生成 (1S,2R,3R,5R)-3-acetoxy-2-methoxycarbonyl-7-oxobicyclo[3.3.0]octane
  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,3R,3aR,4S,6R,6aR)-2,5-Dioxo-octahydro-pentalene-1,3,4,6-tetracarboxylic acid tetramethyl ester 在 phosphate buffer 、 porcine pancreatic lipase Sigma Type II 作用下， 以 甲苯 为溶剂， 反应 336.0h， 以43%的产率得到(3S,3aR,6aS)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,3,4-tricarboxylic acid trimethyl ester
  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