Methanesulfonic acid (1S,2R)-2-hydroxy-1-{(S)-3-hydroxy-3-[(2S,5R,2'R,5'R)-5'-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2'-methyl-octahydro-[2,2']bifuranyl-5-yl]-butyl}-2,6-dimethyl-hept-5-enyl ester | 121401-04-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: Methanesulfonic acid (1S,2R)-2-hydroxy-1-{(S)-3-hydroxy-3-[(2S,5R,2'R,5'R)-5'-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2'-methyl-octahydro-[2,2']bifuranyl-5-yl]-butyl}-2,6-dimethyl-hept-5-enyl ester
• CAS: 121401-04-5
• 化学式: C₃₁H₅₆O₈S
• 分子量: 588.847
• InChiKey: QNKMZLQULDSZTF-PRPYSYEPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.34
• 重原子数：
  40.0
• 可旋转键数：
  15.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  122.52
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  Methanesulfonic acid (1S,2R)-2-hydroxy-1-{(S)-3-hydroxy-3-[(2S,5R,2'R,5'R)-5'-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2'-methyl-octahydro-[2,2']bifuranyl-5-yl]-butyl}-2,6-dimethyl-hept-5-enyl ester 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 0.5h， 生成 (S)-2-((2R,5R,2'S,5'R)-5'-{(S)-1-Hydroxy-1-methyl-3-[(2R,3S)-3-methyl-3-(4-methyl-pent-3-enyl)-oxiranyl]-propyl}-2-methyl-octahydro-[2,2']bifuranyl-5-yl)-6-methyl-hept-5-en-2-ol
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013
• 作为产物：
  描述：

  threo-1,2-epoxy-3,7-dimethy-6-octen-3-ol 在 bis(acetylacetonate)oxovanadium 盐酸 、 叔丁基过氧化氢 、 4-二甲氨基吡啶 、 正丁基锂 、 四甲基乙二胺 、 四丁基氟化铵 、 sodium 、 溶剂黄146 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 二氯甲烷 、 苯 为溶剂， 反应 74.0h， 生成 Methanesulfonic acid (1S,2R)-2-hydroxy-1-{(S)-3-hydroxy-3-[(2S,5R,2'R,5'R)-5'-((S)-1-hydroxy-1,5-dimethyl-hex-4-enyl)-2'-methyl-octahydro-[2,2']bifuranyl-5-yl]-butyl}-2,6-dimethyl-hept-5-enyl ester
  参考文献：
  名称：

  Total synthesis of the meso-triterpene polyether teurilene

  摘要：

  The first total synthesis of the triterpene ether teurilene (1) has been accomplished utilizing two vanadium(V)-catalyzed oxidation-cyclization reactions with different stereoselectivities. The synthesis involved stereoselective and step-by-step construction of 2,5-cis- and 2,5-trans-tetrahydrofuran rings, vanadium(V)-catalyzed oxidation of 4-substituted 4-en-1-ol 40 and subsequent cyclization of the resulting anti-epoxy alcohol 41, and a similar oxidation-cyclization of 5-substituted 4-en-1-ol 49 by way of syn-epoxy alcohol 50. This was followed by construction of a third tetrahydrofuran ring by more conventional means. An improved synthesis of 1, which featured direct formation of bis(tetrahydrofuran) 51 from squalene derivative 66 by simultaneous double oxidation-cyclization, was also accomplished.

  DOI：

  10.1021/jo00007a013