1,2-dioleoyl-3-triphenylmethyl-sn-glycerol | 22202-46-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 三苯基化合物
• 英文名称: 1,2-dioleoyl-3-triphenylmethyl-sn-glycerol
• 英文别名: (Z)-(S)-3-(trityloxy)propane-1,2-diyl dioleate；1-Trityl-sn-gycerol-1,3-dioleat；[(2S)-2-[(Z)-octadec-9-enoyl]oxy-3-trityloxypropyl] (Z)-octadec-9-enoate
• CAS: 22202-46-6
• 化学式: C₅₈H₈₆O₅
• 分子量: 863.318
• InChiKey: XLBJAEZYSMIYLK-XFXRGYTQSA-N

物化性质

• 沸点：
  847.9±65.0 °C(Predicted)
• 密度：
  0.983±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  19.6
• 重原子数：
  63
• 可旋转键数：
  41
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.59
• 拓扑面积：
  61.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  1,2-dioleoyl-3-triphenylmethyl-sn-glycerol 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 以98%的产率得到1,2-二油酰基-sn-甘油
  参考文献：
  名称：

  磷脂酰丝氨酸及其立体异构体的合成：在凝血激活中的作用

  摘要：

  包含两个手性中心的天然磷脂酰丝氨酸（PS）可增强血液凝结。但是，PS增强凝血的过程尚不完全清楚。已经开发出有效且灵活的合成路线来合成PS的所有可能的立体异构体。在这项研究中，我们检查了PS手性中心在调节组织因子（TF）-VIIa凝血起始复合物活性中的作用。全长TF用磷脂酰胆碱重新脂质化，合成的PS异构体分别用于通过FXa生成测定法评估TF-FVIIa复合物的促凝活性。结果表明，由于最佳的蛋白质-脂质相互作用，起始复合物的活性具有立体选择性，并且对PS甘油骨架的构型具有更高的敏感性。

  DOI：

  10.1021/acsmedchemlett.8b00008
• 作为产物：
  描述：

  N-tritylpyridinium tetrafluoroborate 在 4-二甲氨基吡啶 、 锂硼氢 作用下， 以 四氢呋喃 、 氯仿 、 乙腈 为溶剂， 反应 24.0h， 生成 1,2-dioleoyl-3-triphenylmethyl-sn-glycerol
  参考文献：
  名称：

  A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of l-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives

  摘要：

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.

  DOI：

  10.1021/jo990414e

文献信息

• Glycerolipids. III. Stereospecific syntheses of D- and L-1,2-diglycerides via glycerol carbonates
  作者：Francis R. Pfeiffer、C. K. Miao、Jerry A. Weisbach

  DOI：10.1021/jo00826a045

  日期：1970.1.1
• A New Approach to the Stereospecific Synthesis of Phospholipids. The Use of <scp>l</scp>-Glyceric Acid for the Preparation of Diacylglycerols, Phosphatidylcholines, and Related Derivatives
  作者：Farzaneh S. Roodsari、Dongpei Wu、Gregory S. Pum、Joseph Hajdu

  DOI：10.1021/jo990414e

  日期：1999.10.1

  A new stereospecific synthesis of phospholipid derivatives of 1,2-diacyl-sn-glycerols is reported. The synthesis is based on (I) the use of L-glyceric acid as the stereocenter for construction of the optically active phospholipid molecule, (2) preparation of 3-triphenylmethyl-sn-glycerol as the key intermediate for sequential introduction of the primary and secondary acyl functions leading to the chiral diglycerides, and (3) elaboration of the sn-3-phosphodiester headgroup via phosphorylation using 2-chloro-2-oxo-1,3,2-dioxaphospholane, followed by ring opening of the five-membered phosphorus heterocycle with trimethylamine, ammonia, as well as oxygen and sulfur nucleophiles. The sequence has been shown to be suitable for the preparation of both symmetric and mixed-chain diacylglycerols with saturated and unsaturated acyl substituents. Phospholipid headgroups including phosphocholine, phosphoethanolamine, phosphoethanol, and phosphoethylthioacetate functions have been prepared. Application of the method to the synthesis of functionalized phosphatidylcholines has also been demonstrated by incorporating spectroscopically active spin-labeled and fluorescent reporter groups via postsynthetic derivatization of chain terminal w-aminoalkyl functions of the acyl substituents of the compounds. The synthetic methods developed have a great deal of flexibility, providing convenient routes to a wide range of structurally variable phospholipids for physicochemical, enzymological, and cell-biological studies.
• Synthesis of Phosphatidylserine and Its Stereoisomers: Their Role in Activation of Blood Coagulation
  作者：Suman Mallik、Ramesh Prasad、Anindita Bhattacharya、Prosenjit Sen

  DOI：10.1021/acsmedchemlett.8b00008

  日期：2018.5.10

  coagulation. However, the process by which PS enhanced blood coagulation is not completely understood. An efficient and flexible synthetic route has been developed to synthesize all of the possible stereoisomers of PS. In this study, we examined the role of PS chiral centers in modulating the activity of the tissue factor (TF)-factor VIIa coagulation initiation complex. Full length TF was relipidated with

  包含两个手性中心的天然磷脂酰丝氨酸（PS）可增强血液凝结。但是，PS增强凝血的过程尚不完全清楚。已经开发出有效且灵活的合成路线来合成PS的所有可能的立体异构体。在这项研究中，我们检查了PS手性中心在调节组织因子（TF）-VIIa凝血起始复合物活性中的作用。全长TF用磷脂酰胆碱重新脂质化，合成的PS异构体分别用于通过FXa生成测定法评估TF-FVIIa复合物的促凝活性。结果表明，由于最佳的蛋白质-脂质相互作用，起始复合物的活性具有立体选择性，并且对PS甘油骨架的构型具有更高的敏感性。