(2S,6S,10R,14R)-15-((R)-4-Benzyloxymethyl-[1,3]dioxolan-2-yl)-2,6,10,14-tetramethyl-pentadecan-1-ol | 205392-06-9

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (2S,6S,10R,14R)-15-((R)-4-Benzyloxymethyl-[1,3]dioxolan-2-yl)-2,6,10,14-tetramethyl-pentadecan-1-ol
• 英文别名: (2S,6S,10R,14R)-2,6,10,14-tetramethyl-15-[(4R)-4-(phenylmethoxymethyl)-1,3-dioxolan-2-yl]pentadecan-1-ol
• CAS: 205392-06-9
• 化学式: C₃₀H₅₂O₄
• 分子量: 476.74
• InChiKey: HJZAPDIWAQJQMU-LPWNJUKYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  8.8
• 重原子数：
  34
• 可旋转键数：
  19
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 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：

  (2S,6S,10R,14R)-15-((R)-4-Benzyloxymethyl-[1,3]dioxolan-2-yl)-2,6,10,14-tetramethyl-pentadecan-1-ol 在 sodium hydride 、 二异丁基氢化铝 作用下， 以 甲苯 为溶剂， 反应 26.83h， 生成 (2S)-1-[(3R,7R,11S,15S)-16-[(4-methoxyphenyl)methoxy]-3,7,11,15-tetramethylhexadecoxy]-3-phenylmethoxypropan-2-ol
  参考文献：
  名称：

  Total Synthesis of Archaeal 72-Membered Macrocyclic Tetraether Lipids

  摘要：

  Total synthesis of archaeal 72-membered macrocyclic tetraether lipids 3a and 3b is reported. The synthesis was principally composed of preparation of the functionalized half-sized diether compounds 11 and 15 first followed by appropriate dimerization through Julia coupling and final macrocyclization of the crucial dialdehydes 23 and 31 by McMurry coupling. This strategy appeared to be advantageous for the stereoselective synthesis of both natural 72-membered tetraether lipids 3a and 3b using common synthetic intermediates. In addition, this approach was so designed that its synthetic flexibility would allow construction of unnatural structural variants for physicochemical studies. Also described are the results of differential scanning calorimetric analysis of the synthesized lipids 3a and 3b. Both 3a and 3b showed almost the same phase behavior with the broad endothermic phase transition at -53 degrees C. The enthalpy of the phase transition, Delta H, was estimated to be 1.8 and 1.9 kcal/mol for 3a and 3b, respectively. The physicochemical as well as polymorphismic properties of 3a and 3b turned out to be indistinguishable despite of their regioisomeric structures. The physical structure of the phases in terms of the chemical structure is also discussed.

  DOI：

  10.1021/jo972328p
• 作为产物：
  描述：

  (S)-(-)-3-苄氧基-1,2-丙二醇 在 四丁基氟化铵 、 magnesium sulfate 、 对甲苯磺酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 15.5h， 生成 (2S,6S,10R,14R)-15-((R)-4-Benzyloxymethyl-[1,3]dioxolan-2-yl)-2,6,10,14-tetramethyl-pentadecan-1-ol
  参考文献：
  名称：

  Total Synthesis of Archaeal 72-Membered Macrocyclic Tetraether Lipids

  摘要：

  Total synthesis of archaeal 72-membered macrocyclic tetraether lipids 3a and 3b is reported. The synthesis was principally composed of preparation of the functionalized half-sized diether compounds 11 and 15 first followed by appropriate dimerization through Julia coupling and final macrocyclization of the crucial dialdehydes 23 and 31 by McMurry coupling. This strategy appeared to be advantageous for the stereoselective synthesis of both natural 72-membered tetraether lipids 3a and 3b using common synthetic intermediates. In addition, this approach was so designed that its synthetic flexibility would allow construction of unnatural structural variants for physicochemical studies. Also described are the results of differential scanning calorimetric analysis of the synthesized lipids 3a and 3b. Both 3a and 3b showed almost the same phase behavior with the broad endothermic phase transition at -53 degrees C. The enthalpy of the phase transition, Delta H, was estimated to be 1.8 and 1.9 kcal/mol for 3a and 3b, respectively. The physicochemical as well as polymorphismic properties of 3a and 3b turned out to be indistinguishable despite of their regioisomeric structures. The physical structure of the phases in terms of the chemical structure is also discussed.

  DOI：

  10.1021/jo972328p

文献信息

• Total Synthesis of Archaeal 72-Membered Macrocyclic Tetraether Lipids
  作者：Tadashi Eguchi、Kazuya Ibaragi、Katsumi Kakinuma

  DOI：10.1021/jo972328p

  日期：1998.4.1

  Total synthesis of archaeal 72-membered macrocyclic tetraether lipids 3a and 3b is reported. The synthesis was principally composed of preparation of the functionalized half-sized diether compounds 11 and 15 first followed by appropriate dimerization through Julia coupling and final macrocyclization of the crucial dialdehydes 23 and 31 by McMurry coupling. This strategy appeared to be advantageous for the stereoselective synthesis of both natural 72-membered tetraether lipids 3a and 3b using common synthetic intermediates. In addition, this approach was so designed that its synthetic flexibility would allow construction of unnatural structural variants for physicochemical studies. Also described are the results of differential scanning calorimetric analysis of the synthesized lipids 3a and 3b. Both 3a and 3b showed almost the same phase behavior with the broad endothermic phase transition at -53 degrees C. The enthalpy of the phase transition, Delta H, was estimated to be 1.8 and 1.9 kcal/mol for 3a and 3b, respectively. The physicochemical as well as polymorphismic properties of 3a and 3b turned out to be indistinguishable despite of their regioisomeric structures. The physical structure of the phases in terms of the chemical structure is also discussed.