(R)-1-palmitoyl-2-linoleoyl-3-acetylglycerol

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 英文名称: (R)-1-palmitoyl-2-linoleoyl-3-acetylglycerol
• 英文别名: (r)-1-Palmitoyl-2-linoleoyl-3-acetyl-glycerol；[(2R)-1-acetyloxy-3-hexadecanoyloxypropan-2-yl] (9Z,12Z)-octadeca-9,12-dienoate
• 化学式: C₃₉H₇₀O₆
• 分子量: 634.981
• InChiKey: GAKUNXBDVGLOFS-WCCXBCNRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  14.1
• 重原子数：
  45
• 可旋转键数：
  36
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.82
• 拓扑面积：
  78.9
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (R)-1-palmitoyl-3-acetylglycerol 、 (Z,Z)-9,12-十八烷二烯酸二聚物 在 4-二甲氨基吡啶 N,N'-二环己基碳二亚胺 作用下， 以 正己烷 为溶剂， 反应 4.0h， 以81.5%的产率得到(R)-1-palmitoyl-2-linoleoyl-3-acetylglycerol
  参考文献：
  名称：

  [EN] PROCESS FOR REGIOSELECTIVE PREPARATION OF GLYCEROL, DERIVATIVE AND INTERMEDIATE THEREFOR
  [FR] PROCEDE DE PREPARATION STEREOSELECTIVE DE DERIVES DE GLYCEROL ET PRODUITS INTERMEDIAIRES UTILISES DANS CE PROCEDE

  摘要：

  公开了一种用于选择性区域制备l-棕榈酰-2-亚油酰-3-乙酰甘油的过程，该甘油被认为具有促进造血干细胞和巨核细胞增殖的活性，以及用于制备该甘油的中间体。制备l-棕榈酰-2-亚油酰-3-乙酰甘油的过程包括以下步骤：通过将甘油和三烷基正醋酸酯反应得到(2-烷氧基-2-甲基-[1,3]-二氧兰-4-基)甲醇；通过水解(2-烷氧基-2-甲基-[1,3]-二氧兰-4-基)甲醇得到1-乙酰甘油；通过将1-乙酰甘油和棕榈酸衍生物反应得到l-棕榈酰-3-乙酰甘油；通过将l-棕榈酰-3-乙酰甘油和亚油酸衍生物反应得到l-棕榈酰-2-亚油酰-3-乙酰甘油。l-棕榈酰-2-亚油酰-3-乙酰甘油也可以通过以下步骤制备：通过水解棕榈酸(2-烷氧基-2-甲基-[1,3]二氧兰-4-基)甲酯得到l-棕榈酰-3-乙酰甘油；然后将l-棕榈酰-3-乙酰甘油和亚油酸衍生物反应。

  公开号：

  WO2005090274A1

文献信息

• Preparation of glycerol derivatives ad intermediates therefor
  申请人：Lee Tae-Suk

  公开号：US20090253923A1

  公开（公告）日：2009-10-08

  Disclosed is a process for the regioselective preparation of glycerol derivative in a high efficiency and yield. The process for the regioselective preparation of 1-R 1 -2-R 2 -3-acetyl-glycerol derivative comprises the steps of: obtaining 1-R 1 -3-protecting group-glycerol by introducing a protecting group to 3-position of 1-R 1 -glycerol; obtaining 1-R 1 -2-R 2 -3-protecting group-glycerol by introducing R 2 group into 2-position of 1-R 1 -3-protecting group-glycerol; and carrying out the deprotection reaction and the acetylation reaction of 1-R 1 -2-R 2 -3-protecting group-glycerol at the same time. Wherein, R 1 and R 2 are fatty acid groups having 16 to 22 carbon atoms, and are different from each other; and the protecting group is trityl group or trialkylsilyl group.

  揭示了一种高效率和高产率的选择性区域制备甘油衍生物的过程。制备1-R1-2-R2-3-乙酰基甘油衍生物的选择性区域制备过程包括以下步骤：通过在1-R1-甘油的3位引入保护基获得1-R1-3-保护基-甘油；通过在1-R1-3-保护基-甘油的2位引入R2基获得1-R1-2-R2-3-保护基-甘油；同时进行1-R1-2-R2-3-保护基-甘油的去保护反应和乙酰化反应。其中，R1和R2是具有16至22个碳原子的脂肪酸基团，且彼此不同；保护基为三苯基基团或三烷基硅基团。
• METHOD FOR PREPARING MONOACETYGLYCEROLS AND ESTERS THEREOF
  申请人：ENZYCHEM LIFESCIENCES Corporation

  公开号：US20150266803A1

  公开（公告）日：2015-09-24

  Disclosed are a method for preparing 1-acyl-3-acetylglycerol in high purity and high yield without a purification process using a column chromatography, and a method for preparing 1,2-diacyl-3-acetylglycerol in high purity and high yield using the same as a key intermediate. The method includes the steps of: forming a reaction mixture including 1-acyl-3-acetyl glycerol of the Formula 1 in the specification by reacting 1-acylglycerol of the Formula 2 in the specification and an acetylating agent; and separating the racemic or optically active 1-acyl-3-acetylglycerol by crystallizing the reaction mixture in a saturated hydrocarbon solvent having 5 to 7 carbon atoms.

  揭示了一种在高纯度和高产率下制备1-酰基-3-乙酰甘油的方法，无需使用柱层析纯化过程，并且使用相同的方法作为关键中间体制备高纯度和高产率的1,2-二酰基-3-乙酰甘油的方法。该方法包括以下步骤：通过将规范中的1-酰基-3-乙酰甘油的化学式1与规范中的1-酰基甘油的化学式2和乙酰化剂反应形成反应混合物；通过在具有5到7个碳原子的饱和碳氢化合物溶剂中结晶化反应混合物来分离消旋或光学活性的1-酰基-3-乙酰甘油。
• PREPARATION METHOD OF 1-PALMITOYL-3-ACETYLGLYCEROL, AND PREPARATION METHOD OF 1-PALMITOYL-2-LINOLEOYL-3-ACETYLGLYCEROL USING SAME
  申请人：ENZYCHEM LIFESCIENCES CORPORATION

  公开号：US20140243548A1

  公开（公告）日：2014-08-28

  Disclosed are a method for preparing 1-palmitoyl-3-acetylglycerol in high purity and high yield without a purification process using a column chromatography, and a method for preparing 1-palmitoyl-2-linoleoyl-3-acetylglycerol in high purity and high yield using the same as a key intermediate. The method for preparing 1-palmitoyl-3-acetyl glycerol comprises the steps of: forming a reaction mixture including 1-palmitoyl-3-acetyl glycerol of the Formula 1 in the specification by reacting 1-palmitoylglycerol of the Formula 2 in the specification and an acetylating agent; and separating the optically active 1-palmitoyl-3-acetylglycerol by crystallizing the reaction mixture in a saturated hydrocarbon solvent having 5 to 7 carbon atoms.

  本发明公开了一种制备高纯度、高收率的1-棕榈酰-3-乙酰基甘油的方法，无需使用柱层析纯化过程，以及一种利用该方法作为关键中间体制备高纯度、高收率的1-棕榈酰-2-亚麻酰-3-乙酰基甘油的方法。制备1-棕榈酰-3-乙酰基甘油的方法包括以下步骤：通过反应式2中的1-棕榈酰甘油和乙酰化剂反应，形成包括式1中的1-棕榈酰-3-乙酰基甘油的反应混合物；并通过在具有5到7个碳原子的饱和烃溶剂中结晶化反应混合物来分离光学活性的1-棕榈酰-3-乙酰基甘油。
• Preparation of glycerol derivatives and intermediates therefor
  申请人：Enzychem Co., Ltd.

  公开号：US07868196B2

  公开（公告）日：2011-01-11

  Disclosed is a process for the regioselective preparation of glycerol derivative in a high efficiency and yield. The process for the regioselective preparation of 1-R1-2-R2-3-acetyl-glycerol derivative comprises the steps of: obtaining 1-R1-3-protecting group-glycerol by introducing a protecting group to 3-position of 1-R1-glycerol; obtaining 1-R1-2-R2-3-protecting group-glycerol by introducing R2 group into 2-position of 1-R1-3-protecting group-glycerol; and carrying out the deprotection reaction and the acetylation reaction of 1-R1-2-R2-3-protecting group-glycerol at the same time. Wherein, R1 and R2 are fatty acid groups having 16 to 22 carbon atoms, and are different from each other; and the protecting group is trityl group or trialkylsilyl group.

  本发明揭示了一种高效率和高产率的选择区域性制备甘油衍生物的方法。该方法包括以下步骤：通过在1-R1-甘油的3位引入保护基获得1-R1-3-保护基-甘油；通过在1-R1-3-保护基-甘油的2位引入R2基团获得1-R1-2-R2-3-保护基-甘油；同时进行去保护反应和乙酰化反应，以制备1-R1-2-R2-3-乙酰基-甘油衍生物。其中，R1和R2是具有16到22个碳原子的脂肪酸基团，且彼此不同；保护基为三苯甲基基团或三烷基基团。
• PREPARATION OF GLYCEROL DERIVATIVES AND INTERMEDIATES THEREFOR
  申请人：Enzychem Co., Ltd.

  公开号：EP1907345B1

  公开（公告）日：2009-10-21