((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-4-methylenecyclohex-1-en-1-yl)methanol | 1227058-15-2

• 分子结构分类: 有机化合物 - 有机金属化合物 - 有机类金属化合物
• 英文名称: ((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-4-methylenecyclohex-1-en-1-yl)methanol
• CAS: 1227058-15-2
• 化学式: C₂₀H₄₀O₃Si₂
• 分子量: 384.707
• InChiKey: OJUJPIKINFPGGK-QZTJIDSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.65
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  38.69
• 氢给体数：
  1.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  ((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-4-methylenecyclohex-1-en-1-yl)methanol 在 tetra-n-propylammonium perruthenate. 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以545 mg的产率得到(3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-4-methylenecyclohex-1-ene-1-carbaldehyde
  参考文献：
  名称：

  Development of 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor

  摘要：

  In the study of the synthesis of 14-epi-19-norprevitamin D-3, we found 14-epi-19-nortachysterol derivatives through C6,7-cis/trans isomerization. We also succeeded in their chemical synthesis and revealed their marked stability and potent VDR binding affinity. To the best of our knowledge, this is the first isolation of stable tachysterol analogues. Surprisingly, 14-epi-19-nortachysterol derivatives exhibited an unprecedented binding configurations for the ligand binding pocket in hVDR, C5,6-s-trans and C7,8-s-trans triene configurations, which were opposite the natural C7,8-ene-configuration of 1 alpha,25(OH)(2)D-3.

  DOI：

  10.1021/ja201481j
• 作为产物：
  描述：

  methyl (3R,5R)-3,5-bis[(tert-butyldimethylsilyl)oxy]-1-hydroxy-4-methylenecyclohexanecarboxylate 在 吡啶 、 二异丁基氢化铝 、 三氯氧磷 作用下， 以 甲苯 为溶剂， 生成 ((3R,5R)-3,5-bis((tert-butyldimethylsilyl)oxy)-4-methylenecyclohex-1-en-1-yl)methanol
  参考文献：
  名称：

  Development of 14-epi-19-Nortachysterol and Its Unprecedented Binding Configuration for the Human Vitamin D Receptor

  摘要：

  In the study of the synthesis of 14-epi-19-norprevitamin D-3, we found 14-epi-19-nortachysterol derivatives through C6,7-cis/trans isomerization. We also succeeded in their chemical synthesis and revealed their marked stability and potent VDR binding affinity. To the best of our knowledge, this is the first isolation of stable tachysterol analogues. Surprisingly, 14-epi-19-nortachysterol derivatives exhibited an unprecedented binding configurations for the ligand binding pocket in hVDR, C5,6-s-trans and C7,8-s-trans triene configurations, which were opposite the natural C7,8-ene-configuration of 1 alpha,25(OH)(2)D-3.

  DOI：

  10.1021/ja201481j