3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid | 1427278-72-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid
• CAS: 1427278-72-5
• 化学式: C₂₄H₃₅ClO₉
• 分子量: 502.99
• InChiKey: QDOXZJIGVOXHGT-LLNSBFFJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.22
• 重原子数：
  34.0
• 可旋转键数：
  13.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  123.91
• 氢给体数：
  3.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid 在 偶氮二甲酸二异丙酯 、 三苯基膦 作用下， 以 甲苯 为溶剂， 反应 1.5h， 以75%的产率得到(3aR,7S,17S,17aR,E)-13-chloro-10-hydroxy-12-methoxy-17-(methoxymethoxy)-2,2,7-trimethyl-3a,4,5,6,7,16,17,17a-octahydro-9H-benzo[c][1,3]dioxolo[4,5-i][1]oxacyclotetradecin-9-one
  参考文献：
  名称：

  Asymmetric total synthesis of 5′-epi-cochliomycin C

  摘要：

  Asymmetric total synthesis of one of the stereoisomers of naturally occurring chlorine containing 14-membered ring macrolide cochliomycin-F (5'-epi) has been described in this article. The main highlight of the presented synthetic strategy involves a highly regioselective chlorination and Julia-Kocienski olefination with a highly substituted aromatic chloro-aldehyde to create the required E-olefinic unsaturation in the target molecule. Mitsunobu macrolactonization reaction at the late stage enables us to synthesize the target molecule. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.033
• 作为产物：
  描述：

  在 18-冠醚-6 、 lithium hydroxide monohydrate 、 hexaammonium heptamolybdate tetrahydrate 、 四丁基氟化铵 、 双氧水 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 60.0h， 生成 3-chloro-6-hydroxy-2-((S,E)-4-((4R,5R)-5-((R)-4-hydroxypentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-4-(methoxymethoxy)but-1-enyl)-4-methoxybenzoic acid
  参考文献：
  名称：

  Asymmetric total synthesis of 5′-epi-cochliomycin C

  摘要：

  Asymmetric total synthesis of one of the stereoisomers of naturally occurring chlorine containing 14-membered ring macrolide cochliomycin-F (5'-epi) has been described in this article. The main highlight of the presented synthetic strategy involves a highly regioselective chlorination and Julia-Kocienski olefination with a highly substituted aromatic chloro-aldehyde to create the required E-olefinic unsaturation in the target molecule. Mitsunobu macrolactonization reaction at the late stage enables us to synthesize the target molecule. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.02.033