(1S)-methyl 5,6-exo-dihydroxy-3-endo-({(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methylsulfonyl)-1-methoxy-7-oxabicyclo[2.2.1]heptane-2-endo-carboxylate | 409126-07-4

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (1S)-methyl 5,6-exo-dihydroxy-3-endo-({(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methylsulfonyl)-1-methoxy-7-oxabicyclo[2.2.1]heptane-2-endo-carboxylate
• 英文别名: methyl (1S,2R,3S,4S,5S,6R)-5,6-dihydroxy-3-[[(1S,2R,4R)-2-hydroxy-7,7-dimethyl-1-bicyclo[2.2.1]heptanyl]methylsulfonyl]-1-methoxy-7-oxabicyclo[2.2.1]heptane-2-carboxylate
• CAS: 409126-07-4
• 化学式: C₁₉H₃₀O₉S
• 分子量: 434.508
• InChiKey: VTDXTVJSPCCEHQ-GXCNVITRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.7
• 重原子数：
  29
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  148
• 氢给体数：
  3
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  (1S)-methyl 5,6-exo-dihydroxy-3-endo-({(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methylsulfonyl)-1-methoxy-7-oxabicyclo[2.2.1]heptane-2-endo-carboxylate 在 lithium aluminium tetrahydride 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 丙酮 为溶剂， 反应 8.0h， 生成 (1S,2R,4R)-1-((((3aS,4S,5S,6S,7S,7aR)-6-(hydroxymethyl)-7-methoxy-2,2-dimethylhexahydro-4,7-epoxybenzo[d][1,3]dioxol-5-yl)sulfonyl)methyl)-7,7-dimethylbicyclo[2.2.1]heptan-2-ol
  参考文献：
  名称：

  High-Pressure Mediated Asymmetric Diels-Alder Reaction of Chiral Sulfinylacrylate Derivatives and Its Application to Chiral Synthesis of (-)-COTC and (-)-Gabosine C

  摘要：

  The asymmetric Diels-Alder reactions of chiral sulfinylacrylate derivatives (1 and 2) with dienes (3-12) were examined under high-pressure (1.2 GPa) conditions. The endo cycloadduct (13e) obtained from sulfinyl acrylate (1) and 2-methoxyfuran (5) was converted to (-)-COTC (25) and (-)-gabosine C (26).

  DOI：

  10.3987/com-01-s(k)18
• 作为产物：
  描述：

  (1R,2R,3S,4S)-3-((R)-(1S,2R,4R)-2-Hydroxy-7,7-dimethyl-bicyclo[2.2.1]hept-1-ylmethanesulfinyl)-1-methoxy-7-oxa-bicyclo[2.2.1]hept-5-ene-2-carboxylic acid methyl ester 在 四氧化锇 、 十二/十四烷基二甲基氧化胺 作用下， 以 丙酮 为溶剂， 生成 (1S)-methyl 5,6-exo-dihydroxy-3-endo-({(1S,2R,4R)-2-hydroxy-7,7-dimethylbicyclo[2.2.1]heptan-1-yl}methylsulfonyl)-1-methoxy-7-oxabicyclo[2.2.1]heptane-2-endo-carboxylate
  参考文献：
  名称：

  High Pressure Mediated Asymmetric Diels-Alder Reaction of Chiral Sulfinylacrylate Derivatives with Furan and 2-Methoxyfuran

  摘要：

  DOI：

  10.3987/com-95-s43