Methanesulfonic acid (1R,2R,3R,5R)-2-(2S,3aR,6aS)-hexahydro-furo[2,3-b]furan-2-yl-5-isopropenyl-2,3-dimethyl-cyclohexyl ester | 254752-95-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 氧杂环己烷
• 英文名称: Methanesulfonic acid (1R,2R,3R,5R)-2-(2S,3aR,6aS)-hexahydro-furo[2,3-b]furan-2-yl-5-isopropenyl-2,3-dimethyl-cyclohexyl ester
• CAS: 254752-95-9
• 化学式: C₁₈H₃₀O₅S
• 分子量: 358.499
• InChiKey: UCEHFNQBTGGIJN-LWUSAIQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.11
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  61.83
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1R,2R,3R,5R)-2-(2S,3aR,6aS)-hexahydro-furo[2,3-b]furan-2-yl-5-isopropenyl-2,3-dimethyl-cyclohexyl ester 在 lithium carbonate 、 lithium bromide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 以90%的产率得到(3S,4R,6R,2'S,3a'R,6a'S)-3-(hexahydrofuro[2,3-b]furan-2'-yl)-6-isopropenyl-3,4-dimethylcyclohexene
  参考文献：
  名称：

  Total Synthesis of Dihydroclerodin from (R)-(−)-Carvone

  摘要：

  The first total synthesis of the natural enantiomer of the insect-antifeedant dihydroclerodin (1) and lupulin C (40) has been achieved starting from (R)-(-)-carvone (2). In the applied strategy, the hexahydrofuro[2,3-b]furan moiety was introduced in an early stage of the synthesis. The correct configuration at C-9, C-11, C-13, and C-16 was established by application of a remarkably diastereoselective Mukaiyama reaction. The desired configuration at C-10 was obtained by catalytic reduction of the intermediate enone 21. After annulation of the second ring, the structural features at C-4, C-5, and C-6 were introduced. The successful finishing of the synthesis included a Chugaev elimination to give the exocyclic double bond at C-4 that is present in lupulin C. Oxidation of this double bond with m-CPBA afforded dihydroclerodin.

  DOI：

  10.1021/jo991151r
• 作为产物：
  描述：

  (+/-)-cis,trans-(2-methoxytetrahydrofuran-3-yl)methanol 在 吡啶 、 sodium hydroxide 、 trityl perchlorate 、 L-Selectride 、 二异丁基氢化铝 作用下， 以 四氢呋喃 、 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 111.58h， 生成 Methanesulfonic acid (1R,2R,3R,5R)-2-(2S,3aR,6aS)-hexahydro-furo[2,3-b]furan-2-yl-5-isopropenyl-2,3-dimethyl-cyclohexyl ester
  参考文献：
  名称：

  Total Synthesis of Dihydroclerodin from (R)-(−)-Carvone

  摘要：

  The first total synthesis of the natural enantiomer of the insect-antifeedant dihydroclerodin (1) and lupulin C (40) has been achieved starting from (R)-(-)-carvone (2). In the applied strategy, the hexahydrofuro[2,3-b]furan moiety was introduced in an early stage of the synthesis. The correct configuration at C-9, C-11, C-13, and C-16 was established by application of a remarkably diastereoselective Mukaiyama reaction. The desired configuration at C-10 was obtained by catalytic reduction of the intermediate enone 21. After annulation of the second ring, the structural features at C-4, C-5, and C-6 were introduced. The successful finishing of the synthesis included a Chugaev elimination to give the exocyclic double bond at C-4 that is present in lupulin C. Oxidation of this double bond with m-CPBA afforded dihydroclerodin.

  DOI：

  10.1021/jo991151r