(1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-2-ethenyl-1-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclopentan-1-ol | 1114552-64-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: (1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-2-ethenyl-1-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclopentan-1-ol
• CAS: 1114552-64-5
• 化学式: C₂₃H₃₈O₄Si
• 分子量: 406.638
• InChiKey: HZBPNCFEUJJNAC-JDLLUZBXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.18
• 重原子数：
  28
• 可旋转键数：
  9
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.65
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-2-ethenyl-1-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclopentan-1-ol 在 三氧化硫吡啶 作用下， 以 四氢呋喃 为溶剂， 以95%的产率得到(1R,2S,3R,4S)-1-(((4-methoxybenzyl)oxy)methyl)-4-methyl-2-vinylcyclopentane-1,3-diol
  参考文献：
  名称：

  Synthetic Studies toward Jatrophane Diterpenes from Euphorbia characias. Enantioselective Synthesis of (−)-15-O-Acetyl-3-O-propionyl-17-norcharaciol

  摘要：

  The enantioselective synthesis of (+)-17-norcharaciol is described. An uncatalyzed intramolecular carbonyl-ene reaction and a ring-closing metathesis were used as key C/C-connecting transformations to assemble the trans-bicyclo[10.3.0]pentadecane norditerpenoid core. We also report the evolution of our synthetic strategy toward the fully substituted characiol skeleton and the experiences from this venture.

  DOI：

  10.1021/jo802581g
• 作为产物：
  描述：

  methyl (1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-2-ethenyl-1-hydroxy-4-methylcyclopentane-1-carboxylate 在 lithium aluminium tetrahydride 、 四丁基碘化铵 、 sodium hydride 作用下， 以 四氢呋喃 、 二甲基亚砜 、 mineral oil 为溶剂， 反应 14.25h， 生成 (1R,2S,3R,4S)-3-[tert-butyl(dimethyl)silyl]oxy-2-ethenyl-1-[(4-methoxyphenyl)methoxymethyl]-4-methylcyclopentan-1-ol
  参考文献：
  名称：

  Total Synthesis of Natural and Non-Natural Δ^5,6Δ^12,13-Jatrophane Diterpenes and Their Evaluation as MDR Modulators

  摘要：

  We report the details of the total synthesis of natural and non-natural jatropha-5,12-dienes. The successful tactic for the assembly of the strained trans-bicyclo[10.3.0]pentadecane scaffold employed a B-alkyl Suzuki-Miyaura cross-coupling for the formation of the C5/C6 double bond and a ring-closing metathesis for the construction of the C12/C13 double bond. The key step of the synthesis of the cyclopentane fragment, an uncatalyzed intramolecular carbonyl-ene reaction, was studied computationally by DFT calculations. The members of the ensemble of synthetic natural and non-natural jatrophanes were subsequently examined as modulators for the ABCB1, ABCG2, and ABCC1 efflux proteins, which are associated with multidrug resistance in cancer chemotherapy.

  DOI：

  10.1021/jo1019738