<2E,4E,7R,12R,13S>-13-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-12-hydroxy-3,5,7-trimethyltetradeca-2,4-dienedioic acid 1,1-dimethylethyl ester | 145668-57-1

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: <2E,4E,7R,12R,13S>-13-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-12-hydroxy-3,5,7-trimethyltetradeca-2,4-dienedioic acid 1,1-dimethylethyl ester
• 英文别名: [2E,4E,7R,12R,13S]-13-({[(1,1-dimethylethyl)dimethylsilyl]oxy}methyl)-12-hydroxy-3,5,7-trimethyltetradeca-2,4-dienedioic acid 1,1-dimethylethyl ester；(2R,3R,8R,10E,12E)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-3-hydroxy-8,10,12-trimethyl-14-[(2-methylpropan-2-yl)oxy]-14-oxotetradeca-10,12-dienoic acid
• CAS: 145668-57-1
• 化学式: C₂₈H₅₂O₆Si
• 分子量: 512.803
• InChiKey: CNNRPNRGQVQHFR-OBUBVYJWSA-N

物化性质

• 沸点：
  554.4±50.0 °C(Predicted)
• 密度：
  0.992±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  6.89
• 重原子数：
  35
• 可旋转键数：
  17
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.79
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  <2E,4E,7R,12R,13S>-13-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-12-hydroxy-3,5,7-trimethyltetradeca-2,4-dienedioic acid 1,1-dimethylethyl ester 在 吡啶 、 苯磺酰氯 作用下， 反应 18.5h， 以70%的产率得到<2R-<2α,(2E,4E,7R*),3β>>-11-<3-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-4-oxo-2-oxetanyl>-3,5,7-trimethyl-2,4-undecadienoic acid 1,1-dimethylethyl ester
  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：

  [(3R)-7-[(4R,5R)-5-[[tert-butyl(dimethyl)silyl]oxymethyl]-2,2-dimethyl-1,3-dioxan-4-yl]-3-methyl-6-methylsulfonyloxyheptyl] 2,2-dimethylpropanoate 在 palladium diacetate sodium chlorite 、 sodium dihydrogenphosphate 、 二氯二茂锆 、 草酰氯 、 potassium tert-butylate 、 TEMPO⁺Cl^- 、 碘 、 二甲基氯化铝 、 三乙基硼氢化锂 、 二甲基亚砜 、 三乙胺 、 silver carbonate 作用下， 以 四氢呋喃 、 乙醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 13.92h， 生成 <2E,4E,7R,12R,13S>-13-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-12-hydroxy-3,5,7-trimethyltetradeca-2,4-dienedioic acid 1,1-dimethylethyl ester
  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.