1-O-tert-butyldiphenylsilyl-2-O-palmitoyl-rac-glycerol | 572920-43-5

• 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: 1-O-tert-butyldiphenylsilyl-2-O-palmitoyl-rac-glycerol
• CAS: 572920-43-5
• 化学式: C₃₅H₅₆O₄Si
• 分子量: 568.913
• InChiKey: UICVTNFVNSDMOP-UHFFFAOYSA-N

物化性质

• 沸点：
  616.1±55.0 °C(Predicted)
• 密度：
  1.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  7.95
• 重原子数：
  40.0
• 可旋转键数：
  21.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.63
• 拓扑面积：
  55.76
• 氢给体数：
  1.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  1-O-tert-butyldiphenylsilyl-2-O-palmitoyl-rac-glycerol 在 N-溴代丁二酰亚胺(NBS) 、 溴 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 various solvents 、 水 、 二甲基亚砜 为溶剂， 反应 87.25h， 生成 1-hydroxy-2-hexadecanoyl-sn-glycero-3-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 咪唑 、 氢气 作用下， 以 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 72.25h， 生成 1-O-tert-butyldiphenylsilyl-2-O-palmitoyl-rac-glycerol
  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