(2S,4R)-1,2:4,5-diepoxypentane

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 环氧化物
• 英文名称: (2S,4R)-1,2:4,5-diepoxypentane
• 英文别名: (2R)-2-[[(2S)-oxiran-2-yl]methyl]oxirane
• 化学式: C₅H₈O₂
• 分子量: 100.117
• InChiKey: HCPAOTGVQASBMP-SYDPRGILSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  7
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  25.1
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  1,4-戊二烯 在 potassium osmate(VI) 、 氢化奎宁 1,4-(2,3-二氮杂萘)二醚 吡啶 、 sodium hydride 、 potassium carbonate 、 potassium hexacyanoferrate(III) 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 23.0h， 生成 (2S,4R)-1,2:4,5-diepoxypentane
  参考文献：
  名称：

  Enantiospecific Total Synthesis of l-2‘,3‘-Dideoxyisonucleosides via Regioselective Opening of Optically Active C₂-Symmetric 1,4-Pentadiene Bis-epoxide¹

  摘要：

  A new method for the synthesis of L-2',3'-dideoxyisonucleosides is described. The readily available, optically active C-2-symmetric bis-epoxide (2S,4S)-1,2:4,5-diepoxypentane (5) was prepared by a short route from readily available starting materials. The key step of the new synthesis is the opening of 5 with nucleophiles, which proceeds highly regioselectively; e.g., reaction with sodium sulfide affords a 5:1 mixture of the tetrahydrothiophenediol 9a and the tetrahydrothiopyrandiol 14, and reaction with sodium hydroxide gives exclusively the tetrahydrofurandiol 9b via a preferred 5-exo cyclization. These five-membered diols 9a,b can be converted in only four steps into the modified dideoxyuridine and adenosine isonucleosides 4a-c, one of which (4c) has shown good antiviral activity. In addition, we have examined the opening of the analogous six carbon bis-epoxide, (2S,5S)-1,2:5,6-diepoxyhexane (23), which affords a 3:1 mixture of the hexahydrothiepinediol 24 and the tetrahydrothiopyrandiol 25 with sodium sulfide via a preferred 7-endo cyclization. An alternate route to these two optically active bis-epoxides 5 and 23 was also examined, namely the asymmetric dihydroxylation of 1,4-pentadiene and 1,5-hexadiene followed by selective sulfonylation and epoxide : formation. The asymmetric reaction produces a nearly 1:1 mixture of optically active and meso tetrols, e.g., 28-9 and 32-3. Unfortunately, the tetrols, their simple derivatives, and the final sulfonates and epoxides could not be readily separated by Rnv simple means.

  DOI：

  10.1021/jo9721655