1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-3,7,11,15-tetramethylheptadec-16-enyl]-sn-glycerol | 307949-95-7

• 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: 1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-3,7,11,15-tetramethylheptadec-16-enyl]-sn-glycerol
• CAS: 307949-95-7
• 化学式: C₅₁H₉₄O₃
• 分子量: 755.306
• InChiKey: CWZKHLLDPGNZSC-FDVUVBQRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  15.7
• 重原子数：
  54.0
• 可旋转键数：
  38.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.84
• 拓扑面积：
  27.69
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-3,7,11,15-tetramethylheptadec-16-enyl]-sn-glycerol 在 Grubbs catalyst first generation 作用下， 以 二氯甲烷 为溶剂， 反应 33.0h， 以68%的产率得到3,3'-O-[(3R,7R,11S,15S,18S,22S,26R,30R)-3,7,11,15,18,22,26,30-Octamethyldotriacont-16-ene-1,32-diyl]-1,1'-di-O-benzyl-2,2'-di-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-sn-diglycerol
  参考文献：
  名称：

  Giant Vesicles from 72-Membered Macrocyclic Archæal Phospholipid Analogues: Initiation of Vesicle Formation by Molecular Recognition between Membrane Components

  摘要：

  Stereochemically pure archaeal acyclic bola-amphiphilic diphosphates 4 and 5, with the basic structure of the phospholipids found in Sulfolobus, have been synthesized for the first time. The self-assembly properties have been compared with those of the nearly identical 72-membered macrocyclic tetraether phosphates 3a and 3b, analogues of the major phospholipid components of Sulfolobus, Thermoplasma, and methanogenic Archaea, which were also synthesized. Phase contrast and fluorescence microscopies have shown that the dipolar lipids 1 and 2 spontaneously formed vesicles. Whereas the macrocyclic dipolar phosphates 3 spontaneously formed vesicles (phase contrast and fluorescence microscopies), the bolaform phosphate 4 gave only a lamellar structure (synchrotron diffraction pattern: repeat distance of about 4.25 nm but with only a few layers). However, upon addition of the unphosphorylated precursors phytanol, phytol, or geranylgeraniol to the acyclic lipids 4 and 5, giant vesicles were rapidly formed. Addition of n-hexadecanol or cholesterol did not lead to vesicle formation. Therefore it was concluded that this vesicle formation occurs only when the added molecule is closely compatible with the constituents of the lipid layer and can be inserted into the double layer. A slight mismatch (cholesterol or n-hexadecanol/polyprenyl chains) is therefore enough to block the insertion process presumably required for vesicle formation.

  DOI：

  10.1002/1521-3765(20000915)6:18<3351::aid-chem3351>3.0.co;2-4
• 作为产物：
  描述：

  4-Benzyloxymethyl-2-((2R,6R,10R)-2,6,10,14-tetramethyl-pentadecyl)-[1,3]dioxolane 在 正丁基锂 、 草酰氯 、 四丁基氟化铵 、 sodium hydride 、 二异丁基氢化铝 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 二甲基亚砜 、 甲苯 为溶剂， 反应 54.92h， 生成 1-O-Benzyl-2-O-[(3R,7R,11R)-3,7,11,15-tetramethylhexadecanyl]-3-O-[(3R,7R,11S,15S)-3,7,11,15-tetramethylheptadec-16-enyl]-sn-glycerol
  参考文献：
  名称：

  Giant Vesicles from 72-Membered Macrocyclic Archæal Phospholipid Analogues: Initiation of Vesicle Formation by Molecular Recognition between Membrane Components

  摘要：

  Stereochemically pure archaeal acyclic bola-amphiphilic diphosphates 4 and 5, with the basic structure of the phospholipids found in Sulfolobus, have been synthesized for the first time. The self-assembly properties have been compared with those of the nearly identical 72-membered macrocyclic tetraether phosphates 3a and 3b, analogues of the major phospholipid components of Sulfolobus, Thermoplasma, and methanogenic Archaea, which were also synthesized. Phase contrast and fluorescence microscopies have shown that the dipolar lipids 1 and 2 spontaneously formed vesicles. Whereas the macrocyclic dipolar phosphates 3 spontaneously formed vesicles (phase contrast and fluorescence microscopies), the bolaform phosphate 4 gave only a lamellar structure (synchrotron diffraction pattern: repeat distance of about 4.25 nm but with only a few layers). However, upon addition of the unphosphorylated precursors phytanol, phytol, or geranylgeraniol to the acyclic lipids 4 and 5, giant vesicles were rapidly formed. Addition of n-hexadecanol or cholesterol did not lead to vesicle formation. Therefore it was concluded that this vesicle formation occurs only when the added molecule is closely compatible with the constituents of the lipid layer and can be inserted into the double layer. A slight mismatch (cholesterol or n-hexadecanol/polyprenyl chains) is therefore enough to block the insertion process presumably required for vesicle formation.

  DOI：

  10.1002/1521-3765(20000915)6:18<3351::aid-chem3351>3.0.co;2-4