3-triphenylmethyl-L-glycerol | 16975-62-5

• 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: 3-triphenylmethyl-L-glycerol
• 英文别名: (R)-3-(trityloxy)propane-1,2-diol；D-3-O-Triphenylmethylglycerin；3-Trityl-sn-glycerol；L(R)-α-O-Trityl-glycerin；(R)-triphenylmethyl-glycerol；L-α-O-Tritylglycerol；(R)-3-O-Trityl-glycerin；3-O-trityl-sn-glycerol；(2R)-3-trityloxypropane-1,2-diol
• CAS: 16975-62-5
• 化学式: C₂₂H₂₂O₃
• 分子量: 334.415
• InChiKey: WBIMHXTXZQKJIH-OAQYLSRUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  49.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-triphenylmethyl-L-glycerol 在 4-二甲氨基吡啶 作用下， 以 氯仿 为溶剂， 反应 96.0h， 生成 [(2S)-2-[12-[(1,1,1-trichloro-2-methylpropan-2-yl)oxycarbonylamino]dodecanoyloxy]-3-trityloxypropyl] hexadecanoate
  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
• 作为产物：
  描述：

  N-tritylpyridinium tetrafluoroborate 在 锂硼氢 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 24.0h， 生成 3-triphenylmethyl-L-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

• Simple approach to 1-O-protected (R)- and (S)-glycerols from l- and d-arabinose for glycerol nucleic acids (GNA) monomers research
  作者：Bogdan Doboszewski、Piet Herdewijn

  DOI：10.1016/j.tetlet.2011.05.073

  日期：2011.7

  5-O-Protected (-Tr, -Sitert-BuPh2) d- and l-arabinofuranoses easily available in multigram quantities were converted to (S)- and (R)-1-O-protected glycerols, respectively, via oxidation (NaIO4) and reduction (NaBH4). Sources of chirality in the targets are the C4 atoms in the substrates. This stereospecific procedure permits a very simple access to both enantiomeric 1-O-protected glycerols for GNA

  5- O-保护的（-Tr，-Sitert-BuPh 2）d-和1-阿拉伯呋喃糖酶很容易以克数形式通过氧化作用分别转化为（S）和（R）-1- O保护的甘油。 NaIO 4）和还原（NaBH 4）。靶中的手性来源是底物中的C4原子。该立体特异性方法允许非常简单地获得两种对映体1- O-保护的甘油，以用于GNA单体工作。
• 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。
• Synthesis of 1,2-di-O-hexadecanoyl-3-O-(β-<scp>D</scp>-galactopyranosyl)-<scp>L</scp>-glycerol (a ‘galactosyl diglyceride’) and 1,2-di-O-octadecanoyl-3-O-(6-O-octadecanoyl-β-<scp>D</scp>-galactopyranosyl)-<scp>L</scp>-glycerol
  作者：Patricia A. Gent、Roy Gigg

  DOI：10.1039/p19750000364

  日期：——

  6-tetra-O-acetyl-β-D-galactopyranosly)-L-glycerol. This compound was converted into the crystalline 3-O-(2,3,4-tri-O-benzyl-β-D-galactopyranosyl)-L-glycerol, which was used as an intermediate for the synthesis of the title compounds. 3-O-(2,3,4-Tri-O-benzyl-β-D-galactopyranosyl)-L-glycerol is also a potential intermediate for the syntheses of ‘polygalactosyl diglycerides’ which are the serologically active

  将1,2-二-O-苄基-L-甘油（通过3 - O-烯丙基-1,2-二-O-苄基-L-甘油通过新方法制备）糖基化以得到1,2-二- O-苄基-3- O-（2,3,4,6-四-O-乙酰基-β - D-吡喃半乳糖醛）-L-甘油。将该化合物转化为结晶的3 - O-（2,3,4-三-O-苄基-β - D-吡喃并吡喃糖基）-L-甘油，将其用作合成标题化合物的中间体。3- ø - （2,3,4-三- ö-苄基-β - D-吡喃半乳糖基）-L-甘油也是合成``聚半乳糖基甘油二酸酯''的潜在中间体，``聚半乳糖基甘油二酸酯''是肺炎支原体糖脂的血清学活性成分。制备了1,2-双-O-（2-甲基烯丙基）-L-甘油，并尝试将其在β-链中与2,3,4-三-O-苄基-6- O-（丁-2-烯基）-α- d -galactopyranosyl酰氯[由选自烯丙基-6-新途径制备ø - （丁-2-烯基）-α- d -gala
• Chemistry of the lipids
  作者：Y. G. Molotkovskii、L. F. Nikulina、L. D. Bergel'son

  DOI：10.1007/bf00683823

  日期：1969.7

  Conclusions1. A. new route for the synthesis of optically active α,β-diglycerides has been developed.2. D- and L-α, β-Distearins and D-α, β-dilinolenin have been synthesized from the readily accessible L- and D-α-O-tritylglycerols.

  结论 1. A. 开发了合成光学活性α,β-甘油二酯的新路线。2．D-和 L-α, β-二硬脂精和 D-α, β-二亚麻油酸已经从容易获得的 L- 和 D-α-O-三苯甘油酯合成。
• Stereospecific synthesis of ether phospholipids. Preparation of 1-O-(3′-carboxypropyl)-glycero-3-phosphoserine from glyceric acid
  作者：Ranjan P. Srivastava、Joseph Hajdu

  DOI：10.1016/0040-4039(91)80210-w

  日期：1991.11

  A new stereospecific synthesis of carboxyalkyl ether phospholipids is reported.

  报道了羧基烷基醚磷脂的新的立体有择合成。