(1R,2R,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxy-2-hydroxymethyl-bicyclo[3.3.0]octane | 96648-15-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2R,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxy-2-hydroxymethyl-bicyclo[3.3.0]octane
• 英文别名: (3'aalpha,4'alpha,5'beta,6'aalpha)-5'-(((tert-Butyl)dimethylsilyl)oxy)hexahydrospiro(1,3-dioxolane-2,2'(1'H)-pentalene)-4'-methanol；[(1'R,2'S,3'aS,6'aR)-2'-[tert-butyl(dimethyl)silyl]oxyspiro[1,3-dioxolane-2,5'-2,3,3a,4,6,6a-hexahydro-1H-pentalene]-1'-yl]methanol
• CAS: 96648-15-6
• 化学式: C₁₇H₃₂O₄Si
• 分子量: 328.524
• InChiKey: ADRWUKNDQZKRCK-XGUBFFRZSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.16
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2R,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxy-2-hydroxymethyl-bicyclo[3.3.0]octane 在 吡啶 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 23.5h， 生成 (1R,2S,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxy-2-methylbicyclo[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：

  (3aR,6aR)-2,5-Dihydroxy-3,3a,6,6a-tetrahydro-pentalene-1,4-dicarboxylic acid dimethyl ester 在 咪唑 、 盐酸 、 lithium hydroxide 、 三氟甲磺酸三甲基硅酯 、 sodium triethoxyborohydride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 正己烷 、 二氯甲烷 为溶剂， 反应 27.58h， 生成 (1R,2R,3S,5S)-3-tert-butyldimethylsilyloxy-7,7-ethylenedioxy-2-hydroxymethyl-bicyclo[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