<4R-(4α,4(R*),5α)>-5-(hydroxymethyl)-2,2-dimethyl-4-<(4-methyl-1-cyclohexen-1-yl)methyl>-1,3-dioxane

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: <4R-(4α,4(R*),5α)>-5-(hydroxymethyl)-2,2-dimethyl-4-<(4-methyl-1-cyclohexen-1-yl)methyl>-1,3-dioxane
• 英文别名: [4R-(4α,4(R*),5α)]-5-(hydroxymethyl)-2,2-dimethyl-4-[(4-methyl-1-cyclohexen-1-yl)methyl]-1,3-dioxane；[(4R,5R)-2,2-dimethyl-4-[[(4R)-4-methylcyclohexen-1-yl]methyl]-1,3-dioxan-5-yl]methanol
• 化学式: C₁₅H₂₆O₃
• 分子量: 254.37
• InChiKey: BKPBWPBHMLLWCL-IACUBPJLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.87
• 拓扑面积：
  38.7
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  -1-<2-(acetyloxy)-4-<<(1,1-dimethylethyl)dimethylsilyl>oxy>-3-methylene-1-butyl>-4-methylcyclohexene 在 四丁基氟化铵 、 potassium carbonate 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 6.5h， 生成 <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

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.