Hexadecanoic acid (S)-3-hydroxy-2-[12-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-dodecanoyloxy]-propyl ester | 250142-19-9

• 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: Hexadecanoic acid (S)-3-hydroxy-2-[12-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-dodecanoyloxy]-propyl ester
• 英文别名: [(2S)-3-hydroxy-2-[12-[(1,1,1-trichloro-2-methylpropan-2-yl)oxycarbonylamino]dodecanoyloxy]propyl] hexadecanoate
• CAS: 250142-19-9
• 化学式: C₃₆H₆₆Cl₃NO₇
• 分子量: 731.282
• InChiKey: TYMOUALWNNDVSM-HKBQPEDESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  13.2
• 重原子数：
  47
• 可旋转键数：
  34
• 环数：
  0.0
• sp3杂化的碳原子比例：
  0.92
• 拓扑面积：
  111
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  Hexadecanoic acid (S)-3-hydroxy-2-[12-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-dodecanoyloxy]-propyl ester 在 4-二甲氨基吡啶 、 溶剂黄146 、 三乙胺 、 锌 作用下， 以 乙醚 、 二氯甲烷 、 氯仿 、 乙腈 、 苯 为溶剂， 反应 67.5h， 生成 1-palmitoyl-2-[12'-(5"-dimethylaminonaphthalene-1"-sulfonyl)aminolauroyl]-sn-glycero-3-phosphocholine
  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：

  [(2S)-2-[12-[(1,1,1-trichloro-2-methylpropan-2-yl)oxycarbonylamino]dodecanoyloxy]-3-trityloxypropyl] hexadecanoate 在 盐酸 作用下， 以 甲醇 、 氯仿 为溶剂， 反应 18.0h， 以69.5%的产率得到Hexadecanoic acid (S)-3-hydroxy-2-[12-(2,2,2-trichloro-1,1-dimethyl-ethoxycarbonylamino)-dodecanoyloxy]-propyl ester
  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

• 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.