1-Hydroxy-2-tert-butyldimethylsilyl-sn-glycero-3-phosphorylcholine. A useful intermediate in the synthesis of short acyl chain 1-acyl-sn-glycero-3-phosphorylcholines.
The synthesis of 1-acyl-sn-glycero-3-phosphorylcholines in particular those containing short fatty acyl chains are described. The method involves the use of 1-acyl-2-tert-butyl-dimethylsilyl-sn-glycero-3-phosphorylcholines which can be readily prepared by reacting hens' egg yolk 1-acyl-sn-glycero-3-phosphorylcholines with tert-butyldimethylchlorosilane with imidazole as catalyst and dimethylformamide as solvent. Deacylation of the 1-acyl-2-tert-butyldimethylsilyl-sn-glycero-3-phosphorylcholines with saturated anhydrous potassium carbonate in methanol yields the 2-tert-butyldimethylsilyl-sn-glycero-3-phosphorylcholine. Reacylation of the 2-tert-butyldimethylsilyl-sn-glycero-3-phosphorylcholine with fatty acyl anhydride in the presence of 4-dimethylaminopyridine in anhydrous chloroform followed by removal of the tert-butyldimethylsilyl protecting group by treatment with dry hydrogen chloride gas in anhydrous chloroform at 0 degrees yields the desired 1-acyl-sn-glycero-3-phosphorylcholine. Various facets of the reactions involved in developing the synthetic procedures in this study are discussed.
D005997:Glycerylphosphorylcholine / Q000138:chemical synthesis*; D009682:Magnetic Resonance Spectroscopy; D008722:Methods; D009904:Optical Rotation; D010713:Phosphatidylcholines / Q000138:chemical synthesis*; D013055:Spectrophotometry, Infrared
D010713:Phosphatidylcholines; D005997:Glycerylphosphorylcholine