tert-butyl-[[(4R,5S)-2,2-dimethyl-4-[[(4R)-4-methylcyclohexen-1-yl]methyl]-1,3-dioxan-5-yl]methoxy]-dimethylsilane | 145668-43-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: tert-butyl-[[(4R,5S)-2,2-dimethyl-4-[[(4R)-4-methylcyclohexen-1-yl]methyl]-1,3-dioxan-5-yl]methoxy]-dimethylsilane
• CAS: 145668-43-5
• 化学式: C₂₁H₄₀O₃Si
• 分子量: 368.632
• InChiKey: JCUHGVXWTYWYSK-YTQUADARSA-N

物化性质

• 沸点：
  422.7±30.0 °C(predicted)
• 密度：
  0.920±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  25
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 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：

  tert-butyl-[[(4R,5S)-2,2-dimethyl-4-[[(4R)-4-methylcyclohexen-1-yl]methyl]-1,3-dioxan-5-yl]methoxy]-dimethylsilane 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 4.0h， 以95%的产率得到<4R-(4α,4(R*),5α)>-5-(hydroxymethyl)-2,2-dimethyl-4-<(4-methyl-1-cyclohexen-1-yl)methyl>-1,3-dioxane
  参考文献：
  名称：

  Total synthesis of 1233A

  摘要：

  The total synthesis of the HMG-CoA synthase inhibitor 1233A (1), starting from either (R)-pulegone (6) or diketo ester 12, is described. The key transformations included the diastereoselective [2,3] rearrangements of allylic ethers 9 and 19 to alcohols 10 and 11b, respectively, and the diastereoselective hydroboration of 11b to form 19. A Pd-mediated coupling of iodo olefin 31a with tert-butyl crotonate under newly devised conditions provides an efficient preparation of the diene portion of 1233A.

  DOI：

  10.1021/jo00056a013
• 作为产物：
  描述：

  -1-<2-(acetyloxy)-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methylene-1-butyl>-4-methylcyclohexene 在 potassium carbonate 作用下， 以 甲醇 为溶剂， 反应 2.5h， 生成 tert-butyl-[[(4R,5S)-2,2-dimethyl-4-[[(4R)-4-methylcyclohexen-1-yl]methyl]-1,3-dioxan-5-yl]methoxy]-dimethylsilane
  参考文献：
  名称：

  Total synthesis of 1233A

  摘要：

  The total synthesis of the HMG-CoA synthase inhibitor 1233A (1), starting from either (R)-pulegone (6) or diketo ester 12, is described. The key transformations included the diastereoselective [2,3] rearrangements of allylic ethers 9 and 19 to alcohols 10 and 11b, respectively, and the diastereoselective hydroboration of 11b to form 19. A Pd-mediated coupling of iodo olefin 31a with tert-butyl crotonate under newly devised conditions provides an efficient preparation of the diene portion of 1233A.

  DOI：

  10.1021/jo00056a013

文献信息

• Total synthesis of 1233A
  作者：P. M. Wovkulich、K. Shankaran、J. Kiegiel、M. R. Uskokovic

  DOI：10.1021/jo00056a013

  日期：1993.2

  The total synthesis of the HMG-CoA synthase inhibitor 1233A (1), starting from either (R)-pulegone (6) or diketo ester 12, is described. The key transformations included the diastereoselective [2,3] rearrangements of allylic ethers 9 and 19 to alcohols 10 and 11b, respectively, and the diastereoselective hydroboration of 11b to form 19. A Pd-mediated coupling of iodo olefin 31a with tert-butyl crotonate under newly devised conditions provides an efficient preparation of the diene portion of 1233A.