tert-butyl (E,3R,5S)-7-[(1R,5S,6S)-6-(2,2-dimethylbutanoyloxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]-3,5-dihydroxyhept-6-enoate | 144225-46-7

• 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 (E,3R,5S)-7-[(1R,5S,6S)-6-(2,2-dimethylbutanoyloxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]-3,5-dihydroxyhept-6-enoate
• CAS: 144225-46-7
• 化学式: C₂₉H₅₂O₆
• 分子量: 496.728
• InChiKey: YWBAPCKRFDLQCR-SCQVKZRYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  35
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.86
• 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：

  tert-butyl (E,3R,5S)-7-[(1R,5S,6S)-6-(2,2-dimethylbutanoyloxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]-3,5-dihydroxyhept-6-enoate 在 Rh/Al₂O₃ lithium hydroxide 、 氢气 作用下， 以 1,4-二氧六环 、 乙酸乙酯 为溶剂， 反应 5.0h， 生成
  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 4-二甲氨基吡啶 、 氢气 、 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 吡啶 、 甲醇 、 水 、 乙酸乙酯 、 丙酮 为溶剂， -78.0~25.0 ℃ 、101.33 kPa 条件下， 反应 27.5h， 生成 tert-butyl (E,3R,5S)-7-[(1R,5S,6S)-6-(2,2-dimethylbutanoyloxymethyl)-2,2-dimethyl-5-propan-2-ylcyclohexyl]-3,5-dihydroxyhept-6-enoate
  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

文献信息

• C-2 dimethyl seco-mevinic acids. Synthesis of monocyclic HMG-CoA reductase inhibitors from (R)-(-)-carvone.
  作者：Dinesh V. Patel、Robert J. Schmidt、Eric M. Gordon

  DOI：10.1021/jo00052a031

  日期：1992.12

  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.