[(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 | 1026150-09-3

• 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-methyl-6-methylsulfonyloxyheptyl] 2,2-dimethylpropanoate
• CAS: 1026150-09-3
• 化学式: C₂₇H₅₄O₈SSi
• 分子量: 566.872
• InChiKey: ZBLOBJFONCATFA-KYYKXEFOSA-N

物化性质

• 沸点：
  599.6±45.0 °C(Predicted)
• 密度：
  1.018±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  5.91
• 重原子数：
  37
• 可旋转键数：
  16
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  8

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-methyl-6-methylsulfonyloxyheptyl] 2,2-dimethylpropanoate 在 三乙基硼氢化锂 作用下， 以 四氢呋喃 为溶剂， 反应 1.17h， 生成 <4R-(4α,4(R*),5β)>-5-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-β-methyl-2,2-dimethyl-1,3-dioxane-4-heptanol
  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：

  cis-(2R,4R)-2-<<2-<<<(1,1-dimethylethyl)dimethylsilyl>oxy>methyl>-1-prop-2-enyl>oxy>-4-methyl-1-methylenecyclohexane 在 吡啶 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 potassium carbonate 、 臭氧 、 N,N-二异丙基乙胺 、 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 、 正己烷 、 二氯甲烷 为溶剂， 反应 11.25h， 生成 [(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
  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.