(3R)-7-[(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxan-4-yl]-3-methylheptanal | 145668-52-6

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (3R)-7-[(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxan-4-yl]-3-methylheptanal
• CAS: 145668-52-6
• 化学式: C₂₁H₄₂O₄Si
• 分子量: 386.648
• InChiKey: IFVVHQHLMJJQNM-GUDVDZBRSA-N

物化性质

• 沸点：
  446.3±30.0 °C(predicted)
• 密度：
  0.912±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.56
• 重原子数：
  26
• 可旋转键数：
  11
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.95
• 拓扑面积：
  44.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3R)-7-[(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxan-4-yl]-3-methylheptanal 在 二氯二茂锆 、 potassium tert-butylate 、 碘 作用下， 以 四氢呋喃 为溶剂， 反应 7.33h， 生成 <1E,4R,9R,10R>-10-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-2,4-dimethyl-1-iodoundec-1-ene-9,11-diol
  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：

  <4R-(4α,4(R*),5β)>-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-β-methyl-2,2-dimethyl-1,3-dioxane-4-heptanol 在 草酰氯 、 二甲基亚砜 作用下， 生成 (3R)-7-[(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxan-4-yl]-3-methylheptanal
  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.