tert-butyl 2-[(4R,6S)-6-[(E)-2-[(1R,5S,6S)-6-(hydroxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]ethenyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate | 144225-44-5

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: tert-butyl 2-[(4R,6S)-6-[(E)-2-[(1R,5S,6S)-6-(hydroxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]ethenyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate
• CAS: 144225-44-5
• 化学式: C₂₆H₄₆O₅
• 分子量: 438.648
• InChiKey: UCEAZNJIWNIUPU-ZQRYYBCQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.5
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.88
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 2-[(4R,6S)-6-[(E)-2-[(1R,5S,6S)-6-(hydroxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]ethenyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate 在 Rh/Al₂O₃ 4-二甲氨基吡啶 、 氢气 、 对甲苯磺酸 作用下， 以 吡啶 、 甲醇 、 水 、 乙酸乙酯 为溶剂， 反应 19.0h， 生成 tert-butyl (3R,5R)-7-[(1R,5S,6S)-6-(2,2-dimethylbutanoyloxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]-3,5-dihydroxyheptanoate
  参考文献：
  名称：

  C-2 dimethyl seco-mevinic acids. Synthesis of monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone.

  摘要：

  An efficient preparation of novel monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone is reported. Utilizing this chiral carbon pool, the C-2 dimethyl seco-mevinic acid 3a was prepared in 17 steps and 5.2 % overall yield. The key chiral intermediate aldehyde 10a was prepared via a short and efficient synthetic sequence (six steps, 27% yield) from (R)-(-)-carvone. The appropriate chirality of the diol acid side chain was secured by employing the chiral acetate synthon ''(S)-HYTRA'' and by performing a stereoselective 1,3-syn reduction on the beta-hydroxy ketone 19. Structural requirements at the C-2 position are rather stringent, and deletion of or addition of an extra methyl group are both unacceptable modifications for this novel class of monocyclic HMG-CoA reductase inhibitors.

  DOI：

  10.1021/jo00052a031
• 作为产物：
  描述：

  methyl (E,3S)-5-[(1R,5S,6S)-2,2-dimethyl-6-(phenylmethoxymethyl)-5-propan-2-ylcyclohexyl]-3-hydroxypent-4-enoate 在 palladium dihydroxide 氢气 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 乙酸乙酯 、 丙酮 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 11.5h， 生成 tert-butyl 2-[(4R,6S)-6-[(E)-2-[(1R,5S,6S)-6-(hydroxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]ethenyl]-2,2-dimethyl-1,3-dioxan-4-yl]acetate
  参考文献：
  名称：

  C-2 dimethyl seco-mevinic acids. Synthesis of monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone.

  摘要：

  An efficient preparation of novel monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone is reported. Utilizing this chiral carbon pool, the C-2 dimethyl seco-mevinic acid 3a was prepared in 17 steps and 5.2 % overall yield. The key chiral intermediate aldehyde 10a was prepared via a short and efficient synthetic sequence (six steps, 27% yield) from (R)-(-)-carvone. The appropriate chirality of the diol acid side chain was secured by employing the chiral acetate synthon ''(S)-HYTRA'' and by performing a stereoselective 1,3-syn reduction on the beta-hydroxy ketone 19. Structural requirements at the C-2 position are rather stringent, and deletion of or addition of an extra methyl group are both unacceptable modifications for this novel class of monocyclic HMG-CoA reductase inhibitors.

  DOI：

  10.1021/jo00052a031