3-(triphenylmethyl)glyceric acid methyl ester | 111247-96-2

• 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)glyceric acid methyl ester
• 英文别名: 3-triphenylmethyl-L-glyceric acid methyl ester；(S)-methyl 2-hydroxy-3-(trityloxy)propanoate；methyl (2S)-2-hydroxy-3-(triphenylmethoxy)propanoate；methyl (S)-2-hydroxy-3-(trityloxy)propanoate；Methyl-L-3-tritylglycerat；methyl (2S)-2-hydroxy-3-trityloxypropanoate
• CAS: 111247-96-2
• 化学式: C₂₃H₂₂O₄
• 分子量: 362.425
• InChiKey: HTTQDZDTEQMRIJ-NRFANRHFSA-N

物化性质

• 沸点：
  515.2±45.0 °C(Predicted)
• 密度：
  1.182±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  55.8
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  3-(triphenylmethyl)glyceric acid methyl ester 在 四丁基氟化铵 、 silver trifluoroacetate 作用下， 以 四氢呋喃 为溶剂， 生成
  参考文献：
  名称：

  Asymmetric synthesis of RK-682 and its analogs, and evaluation of their protein phosphatase inhibitory activities

  摘要：

  We report an asymmetric synthesis of a potent tyrosine phosphatase inhibitor, RK-682 and its analogs. The absolute stereochemistry of RK-682 was determined to be (R). The inhibitory activities of RK-682 and its analogs, (R)-1a, (S)-1a, (R)-1b and (R)-1c toward various protein phosphatases (MIR, cdc25A, cdc25B, and PP1) are also reported. Copyright (C) 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)02029-1
• 作为产物：
  描述：

  （s）-2,3-二羟基丙酸甲酯 、 三苯基氯甲烷 在 四丁基碘化铵 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 18.0h， 以86%的产率得到3-(triphenylmethyl)glyceric acid methyl ester
  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

文献信息

• [EN] ARYLMETHYLENE HETEROCYCLIC COMPOUNDS AS KV1.3 POTASSIUM SHAKER CHANNEL BLOCKERS<br/>[FR] COMPOSÉS HÉTÉROCYCLIQUES D'ARYLMÉTHYLÈNE UTILISÉS EN TANT QUE BLOQUEURS DES CANAUX POTASSIQUES KV1.3 DE TYPE SHAKER
  申请人：DE SHAW RES LLC

  公开号：WO2021071806A1

  公开（公告）日：2021-04-15

  A compound of Formula (I) or a pharmaceutically acceptable salt thereof is described, wherein the substituents are as defined herein. Pharmaceutical compositions comprising the same and method of using the same are also described.

  描述了化合物的公式（I）或其药学上可接受的盐，其中取代基如本文所定义。还描述了包含相同化合物的药物组合物以及使用该药物的方法。
• A new approach to the synthesis of ether phospholipids. Preparation of 1,2-dialkylglycerophosphorylcholines from L-glyceric acid
  作者：Suresh K Bhatia、Joseph Hajdu

  DOI：10.1016/s0040-4039(00)95704-6

  日期：1987.1

  A novel stereospecific synthesis of antitumor active ether phospholipids is reported.

  报道了抗肿瘤活性醚磷脂的新型立体有择合成。
• 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。
• [EN] PHOSPHOLIPID COMPOUNDS AND USES THEREOF<br/>[FR] COMPOSÉS PHOSPHOLIPIDIQUES ET LEURS UTILISATIONS
  申请人：GILEAD SCIENCES INC

  公开号：WO2022081973A1

  公开（公告）日：2022-04-21

  Compounds and methods of using said compounds, alone or in combination with additional agents, and pharmaceutical compositions of said compounds for the treatment of viral infections are disclosed.

  本文披露了用于治疗病毒感染的化合物及其使用方法，可以单独使用或与其他药物联合使用，并且还包括该化合物的药物组合物。
• 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.