1-棕榈酰-3-O-苄基-外消旋-甘油 | 1487-51-0

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 甘油脂
• 中文名称: 1-棕榈酰-3-O-苄基-外消旋-甘油
• 英文名称: 1-O-benzyl-3-O-palmitoyl-rac-glycerol
• 英文别名: 3-O-benzyl-1-palmitoylglycerol；1-benzyloxy-3-palmitoyloxy-propan-2-ol；DL-α-Benzyl-α'-palmitoyl-glycerin；1-O-Benzyl-3-palmitoyl-rac-glycerin；1-Palmitoyl-3-O-benzyl-rac-glycerol；(2-hydroxy-3-phenylmethoxypropyl) hexadecanoate
• CAS: 1487-51-0
• 化学式: C₂₆H₄₄O₄
• 分子量: 420.633
• InChiKey: KTMANQJLYZAYIP-UHFFFAOYSA-N

物化性质

• 熔点：
  20.5-21 °C
• 沸点：
  532.5±40.0 °C(Predicted)
• 密度：
  0.984±0.06 g/cm3(Predicted)
• 溶解度：
  氯仿（微溶）、乙酸乙酯（微溶）

计算性质

• 辛醇/水分配系数(LogP)：
  8.2
• 重原子数：
  30
• 可旋转键数：
  21
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.73
• 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：

  1-棕榈酰-3-O-苄基-外消旋-甘油 在 palladium on activated charcoal 氢气 、 溴 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 甲醇 、 various solvents 为溶剂， 反应 28.25h， 生成 1-lyso-3-O-palmitoyl-rac-glycero-2-phosphocholine
  参考文献：
  名称：

  Synthesis of 1-lyso-2-palmitoyl-rac-glycero-3-phosphocholine and its regioisomers and structural elucidation by NMR spectroscopy and FAB tandem mass spectrometry

  摘要：

  Three regioisomers of a naturally occurring lysophosphatidylcholine were chemically synthesized from glycerol. The phosphocholine moiety of the molecule was introduced by sequentially reacting with ethylene chlorophosphite, bromine, water, and trimethyl amine. Removal of a silyl protecting group of the hydroxyl group in the glycerol backbone was achieved without any accompanying acyl migration in the final stage of the synthesis by using NBS in a dimethyl sulfoxide-water cosolvent system. Structures of all regioisomers were compared by NMR spectroscopy and FAB tandem mass spectrometry. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00282-5
• 作为产物：
  描述：

  2-O-palmitoyl-1,3-O-benzylideneglycerol 在 palladium on activated charcoal 氢气 、 silver(l) oxide 作用下， 以 二氯甲烷 、 乙酸乙酯 为溶剂， 反应 77.0h， 生成 1-棕榈酰-3-O-苄基-外消旋-甘油
  参考文献：
  名称：

  Synthesis of 1-lyso-2-palmitoyl-rac-glycero-3-phosphocholine and its regioisomers and structural elucidation by NMR spectroscopy and FAB tandem mass spectrometry

  摘要：

  Three regioisomers of a naturally occurring lysophosphatidylcholine were chemically synthesized from glycerol. The phosphocholine moiety of the molecule was introduced by sequentially reacting with ethylene chlorophosphite, bromine, water, and trimethyl amine. Removal of a silyl protecting group of the hydroxyl group in the glycerol backbone was achieved without any accompanying acyl migration in the final stage of the synthesis by using NBS in a dimethyl sulfoxide-water cosolvent system. Structures of all regioisomers were compared by NMR spectroscopy and FAB tandem mass spectrometry. (C) 2003 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4020(03)00282-5

文献信息

• A general protocol for the preparation of phospholipids via phosphite coupling
  作者：Stephen F. Martin、John A. Josey

  DOI：10.1016/s0040-4039(00)82140-1

  日期：——

  A method for the facile preparation of a variety of phospholipids and their derivatives has been developed that utilizes a highly efficient phosphite coupling procedure for the synthesis of a phosphite triester, which may then be readily transformed into the corresponding phosphate diester by sequential oxidation and O-deprotection.

  已开发出一种简便的制备多种磷脂及其衍生物的方法，该方法利用高效的亚磷酸酯偶联步骤合成亚磷酸三酯，然后可以通过顺序氧化和O-转化为相应的磷酸二酯。脱保护。
• Volkova,L.V. et al., Journal of general chemistry of the USSR, 1965, vol. 35, p. 547 - 550
  作者：Volkova,L.V. et al.

  DOI：——

  日期：——
• Baylis et al., 2. Int. Conf. Biochem. Probl. Lipids Gent 1955 S. 91, 92
  作者：Baylis et al.

  DOI：——

  日期：——
• [F-18]labeling of 1,2-diacylglycerols
  作者：Toshihiro Takahashi、Tatsuo Ido、Shinji Nagata、Ren Iwata

  DOI：10.1002/1099-1344(200008)43:9<943::aid-jlcr379>3.0.co;2-v

  日期：2000.8

  We have developed two kinds of [F-18]labeled 1,2-diacylglycerols (1,2-DAGs) such as 1-(omega-[F-18]fluoroacyl)-2-acylglycerols (1*,2-[F-18]FDAGs) and 2-(omega-[F-18]fluoroacyl)-1-acylglycerols (1,2*-[F-18]FDAGs) for imaging receptor-mediated phosphatidyl-inositol (PI) turnover responses by positron emission tomography (PET). The 1*,2-[F-18]FDAGs were synthesized by the reaction of 2-monoacyl glycerols with omega-[F-18]fluoroacyl chlorides (method A) and 1-(16-[F-18]fluoro palmitoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C16,C16)) and 1-(8-[F-18]fluoro octanoyl)-2-palmitoylglycerol (1*,2-[F-18]FDAG(C8,C16)) were synthesized using method A. However, during the synthesis of 1,2*-[F-18]FDAGs, we adopted the hydrogenolysis to remove a benzyl group from 3-O-benzyl-2-(omega-[F-18]fluoroacyl)-1-acylglycerol, which was synthesized by the nucleophilic exchange reaction of 3-O-benzyl-2-(omega-bromoacyl)-1-acylglycerol with [F-18]F- (method B) and 2-(16-[F-18]fluoropalmitoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C16)) and [F-18]fluorooctanoyl)-1-palmitoylglycerol (1,2*-[F-18]FDAG(C16,C8)) were produced using method B. The purified 1*,2-[F-18]FDAGs were obtained in radiochemical yields of 8-35 % (based on [F-18]F-) with radiochemical purities of > 97 % and the purified 1,2*-[F-18]FDAGs were in radiochemical yields of 5-15 % with radiochemical purities of > 95 %. The total synthesis time from the start of the reactive [F-18]F- production, including HPLC purification, was 100 - 135 min (method A) and 115 - 175 min (method B), respectively. It has already been used for more than 100 preparations of 1*,2-[F-18]FDAG(C16,C16), 1*,2-[F-18]FDAG(C8, C16), and 1,2*-[F-18]FDAG(C16,C16), 1,2*-[F-18]FDAG(C16,C8) for animal studies.
• Baylis et al., 1955, p. 91,92
  作者：Baylis et al.

  DOI：——

  日期：——