(3aR,5R,6S,6aR)-5-ethenyl-2,2-dimethyl-6-prop-2-enyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole | 932020-01-4

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3aR,5R,6S,6aR)-5-ethenyl-2,2-dimethyl-6-prop-2-enyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
• CAS: 932020-01-4
• 化学式: C₁₂H₁₈O₃
• 分子量: 210.273
• InChiKey: ZXPIWKDVCUSMHE-LNFKQOIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  15
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  27.7
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  (3aR,5R,6S,6aR)-5-ethenyl-2,2-dimethyl-6-prop-2-enyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole 在 Grubbs catalyst first generation sodium hydroxide 、 四(三苯基膦)钯 、 硫酸 、 sodium hydride 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 二甲基亚砜 、 乙腈 为溶剂， 反应 62.75h， 生成 (-)-卡巴韦
  参考文献：
  名称：

  A short and efficient synthesis of 5-hydroxymethylcyclopent-2-enol from d-glucose and its elaboration to the carbanucleoside (−)-carbovir

  摘要：

  Introduction of an allyl functionality at C-3 of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose followed by olefination at C-5 and C-6 provided 1,6-diene 5 which, upon ring closing metathesis and subsequent functional group manipulation, furnished the key cyclopentene diacetate 7, which was elaborated to carbanucleoside (-)-carbovir 1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.016
• 作为产物：
  描述：

  1,2,5,6-di-O-isopropylidene-α-D-glucofuranose-3-O-(S-methylxanthate) 在 偶氮二异丁腈 、 溶剂黄146 作用下， 以 甲苯 为溶剂， 反应 17.5h， 生成 (3aR,5R,6S,6aR)-5-ethenyl-2,2-dimethyl-6-prop-2-enyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxole
  参考文献：
  名称：

  A short and efficient synthesis of 5-hydroxymethylcyclopent-2-enol from d-glucose and its elaboration to the carbanucleoside (−)-carbovir

  摘要：

  Introduction of an allyl functionality at C-3 of 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose followed by olefination at C-5 and C-6 provided 1,6-diene 5 which, upon ring closing metathesis and subsequent functional group manipulation, furnished the key cyclopentene diacetate 7, which was elaborated to carbanucleoside (-)-carbovir 1. (c) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.01.016