(-)-methyl (3R,4E,6E,11S)-3,11-dihydroxydodeca-4,6-dienoate | 1610558-07-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (-)-methyl (3R,4E,6E,11S)-3,11-dihydroxydodeca-4,6-dienoate
• CAS: 1610558-07-0
• 化学式: C₁₃H₂₂O₄
• 分子量: 242.315
• InChiKey: GVJKTSZFVVRYJO-UFFRUMCTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.57
• 重原子数：
  17.0
• 可旋转键数：
  8.0
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  66.76
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (-)-methyl (3R,4E,6E,11S)-3,11-dihydroxydodeca-4,6-dienoate 在 水 、 lithium hydroxide 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 2.0h， 以91%的产率得到(-)-ieodomycin C
  参考文献：
  名称：

  Stereoselective total synthesis of ieodomycin C

  摘要：

  A concise stereoselective synthesis of the marine natural product ieodomycin C (3) has been achieved from commercially available pyridinium-1-sulfonate (8) in eight linear steps and 14% overall yield. The key synthetic steps included a B-alkyl Suzuki-Miyaura cross-coupling reaction and an Evans-Nagao acetate aldol reaction. The same synthetic sequence was used for preparing the enantiomer of ieodomycin C (3). Our efforts confirmed the structure of the antibacterial natural product 3. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.020
• 作为产物：
  描述：

  (+)-methyl (3R,4E,6E,11S)-3,11-bis((tert-butyldimethylsilyl)oxy)dodeca-4,6-dienoate 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 48.0h， 以57%的产率得到(-)-methyl (3R,4E,6E,11S)-3,11-dihydroxydodeca-4,6-dienoate
  参考文献：
  名称：

  Stereoselective total synthesis of ieodomycin C

  摘要：

  A concise stereoselective synthesis of the marine natural product ieodomycin C (3) has been achieved from commercially available pyridinium-1-sulfonate (8) in eight linear steps and 14% overall yield. The key synthetic steps included a B-alkyl Suzuki-Miyaura cross-coupling reaction and an Evans-Nagao acetate aldol reaction. The same synthetic sequence was used for preparing the enantiomer of ieodomycin C (3). Our efforts confirmed the structure of the antibacterial natural product 3. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2014.04.020