(11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol | 332842-86-1

• 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: (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol
• CAS: 332842-86-1
• 化学式: C₂₅H₄₂O₅
• 分子量: 422.605
• InChiKey: QGKHYRJGRSASJE-YXKGSVJHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  30.0
• 可旋转键数：
  15.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  68.15
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol 、 2,2-二甲氧基丙烷 在 对甲苯磺酸 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 (4E)-1-{(1R)-1-[6-((1R)-1-{[(4-methoxyphenyl)methoxy]methyl}propyl)(6S,4R)-2,2-dimethyl(1,3-dioxan-4-yl)]ethyl}(2S,1R)-1-methoxy-2-methylhex-4-ene
  参考文献：
  名称：

  Total Synthesis of the Immunosupressant (−)-Pironetin (PA48153C)

  摘要：

  [GRAPHICS]Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned, Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition, a highly selective Lewis acid promoted Mukaiyama aldol reaction, an anti-selective Sml(2) reduction of a beta -hydroxyketone, and finally a lactone annulation reaction.

  DOI：

  10.1021/ol015531m
• 作为产物：
  描述：

  (E)-(2R,3R,4S)-3-Methoxy-2,4-dimethyl-oct-6-enal 在 samarium diiodide 、 三氟化硼乙醚 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 15.0h， 生成 (11E)(4S,7S,9S,3R,6R,8R)-8-methoxy-3-{[(4-methoxyphenyl)methoxy]methyl}-7,9-dimethyltridec-11-ene-4,6-diol
  参考文献：
  名称：

  Total Synthesis of the Immunosupressant (−)-Pironetin (PA48153C)

  摘要：

  [GRAPHICS]Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials and the desired structure are readily discerned, Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition, a highly selective Lewis acid promoted Mukaiyama aldol reaction, an anti-selective Sml(2) reduction of a beta -hydroxyketone, and finally a lactone annulation reaction.

  DOI：

  10.1021/ol015531m