ethyl (3aS,3bR,4aS,5S,5aR)-5-(1,3-dithian-2-yl)-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole-3b(3aH)-carboxylate | 1069040-62-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: ethyl (3aS,3bR,4aS,5S,5aR)-5-(1,3-dithian-2-yl)-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole-3b(3aH)-carboxylate
• CAS: 1069040-62-5
• 化学式: C₁₆H₂₄O₄S₂
• 分子量: 344.496
• InChiKey: BLLQABJRPUZDAT-GBNBPPIOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  22.0
• 可旋转键数：
  3.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.94
• 拓扑面积：
  44.76
• 氢给体数：
  0.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  ethyl (3aS,3bR,4aS,5S,5aR)-5-(1,3-dithian-2-yl)-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole-3b(3aH)-carboxylate 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 1.0h， 以36%的产率得到(1R,2S,4S,5S,3R)-1-ethoxycarbonyl-4-formyl-2,3-O-isopropylidene-2,3-dihydroxybicyclo[3.1.0]hexane
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure (S)-Methanocarbaribo Uracil Nucleoside Derivatives for Use as Antiviral Agents and P2Y Receptor Ligands

  摘要：

  We have developed an approach toward enantiomerically pure (S)-methanocarba ribonucleosides based on several functional group transformations on a sensitive bicyclo[3.1.0]-hexane system. D-Ribose was transformed into methanocarba alcohol 3 followed by conversion of the OH group to a nitrile with inversion of configuration at C4. The nitrile group was subsequently reduced in two stages to the 5'-hydroxymethyl group. An ester group appended to a tertiary carbon (Cl) was transformed to an amino group as a nucleobase precursor.

  DOI：

  10.1021/jo801224j
• 作为产物：
  描述：

  1,3-二噻烷 、 ethyl (1R,2S,3R,4R,5R)-2-hydroxy-3,4-isopropylenedioxybicyclo[3.1.0]hexane-1-carboxylate 在 三氟甲磺酸 、 吡啶 、 trifluoromethanesulfonic acid anhydride 、 六甲基磷酰三胺 、 正丁基锂 作用下， 以 二氯甲烷 、 四氢呋喃 、 正己烷 为溶剂， 反应 0.34h， 以121 mg的产率得到ethyl (3aS,3bR,4aS,5S,5aR)-5-(1,3-dithian-2-yl)-2,2-dimethyltetrahydrocyclopropa[3,4]cyclopenta[1,2-d][1,3]dioxole-3b(3aH)-carboxylate
  参考文献：
  名称：

  Synthesis of Enantiomerically Pure (S)-Methanocarbaribo Uracil Nucleoside Derivatives for Use as Antiviral Agents and P2Y Receptor Ligands

  摘要：

  We have developed an approach toward enantiomerically pure (S)-methanocarba ribonucleosides based on several functional group transformations on a sensitive bicyclo[3.1.0]-hexane system. D-Ribose was transformed into methanocarba alcohol 3 followed by conversion of the OH group to a nitrile with inversion of configuration at C4. The nitrile group was subsequently reduced in two stages to the 5'-hydroxymethyl group. An ester group appended to a tertiary carbon (Cl) was transformed to an amino group as a nucleobase precursor.

  DOI：

  10.1021/jo801224j