(S)-4-Hydroxy-5-[(2S,4S,6R)-6-((R)-2-hydroxy-3,3-dimethyl-4-oxo-pentyl)-2-(4-methoxy-phenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]-3,3-dimethyl-pentan-2-one | 268750-45-4

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (S)-4-Hydroxy-5-[(2S,4S,6R)-6-((R)-2-hydroxy-3,3-dimethyl-4-oxo-pentyl)-2-(4-methoxy-phenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]-3,3-dimethyl-pentan-2-one
• CAS: 268750-45-4
• 化学式: C₂₇H₄₂O₇
• 分子量: 478.626
• InChiKey: NFIGPWIXSUDFGX-PFYGBQHCSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.24
• 重原子数：
  34.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  102.29
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (S)-4-Hydroxy-5-[(2S,4S,6R)-6-((R)-2-hydroxy-3,3-dimethyl-4-oxo-pentyl)-2-(4-methoxy-phenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]-3,3-dimethyl-pentan-2-one 在 氯代二环己基硼烷 、 三乙胺 、 tetramethylammonium triacetoxyborohydride 作用下， 以 乙醚 、 丙酮 为溶剂， 反应 147.0h， 生成 (3S,5S,7R)-8-[(2S,4R,6S)-6-[(2S,4R,6R)-4,6-Dihydroxy-2,8-bis-(4-methoxy-benzyloxy)-3,3,7,7-tetramethyl-octyl]-2-(4-methoxy-phenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]-1,7-bis-(4-methoxy-benzyloxy)-2,2,6,6-tetramethyl-octane-3,5-diol
  参考文献：
  名称：

  Stereoselective Synthesis of Skipped Polyols by Substrate-Directed Asymmetric Induction

  摘要：

  A series of C-2- or sigma-symmetric oligo-1,3-dioxanylmethanes, 2-5, have been prepared using a bidirectional approach. In bidirectional syntheses of meso compounds, only substrate-based asymmetric induction could be applied. 1,3-Asymmetric induction in Mukaiyama-aldol additions, 1,5-asymmetric induction in enol-borinate aldol reactions, and 1,3-anti-selective reduction of aldols turned out to be reliable tools in the preparation of compounds 3-5.

  DOI：

  10.1021/ol0056325
• 作为产物：
  描述：

  4-甲氧基苯甲醛二乙基缩醛 在 camphor-10-sulfonic acid 、 三氟化硼乙醚 、 臭氧 作用下， 以 二氯甲烷 为溶剂， 反应 14.0h， 生成 (S)-4-Hydroxy-5-[(2S,4S,6R)-6-((R)-2-hydroxy-3,3-dimethyl-4-oxo-pentyl)-2-(4-methoxy-phenyl)-5,5-dimethyl-[1,3]dioxan-4-yl]-3,3-dimethyl-pentan-2-one
  参考文献：
  名称：

  Stereoselective Synthesis of Skipped Polyols by Substrate-Directed Asymmetric Induction

  摘要：

  A series of C-2- or sigma-symmetric oligo-1,3-dioxanylmethanes, 2-5, have been prepared using a bidirectional approach. In bidirectional syntheses of meso compounds, only substrate-based asymmetric induction could be applied. 1,3-Asymmetric induction in Mukaiyama-aldol additions, 1,5-asymmetric induction in enol-borinate aldol reactions, and 1,3-anti-selective reduction of aldols turned out to be reliable tools in the preparation of compounds 3-5.

  DOI：

  10.1021/ol0056325