A short, general synthesis of glycerophospholipids

✍ Scribed by R. Aneja; J.S. Chadha; A.P. Device

• Book ID: 104239975
• Publisher: Elsevier Science
• Year: 1969
• Tongue: French
• Weight: 218 KB
• Volume: 10
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)88649-4

✦ Synopsis

The biologically important monoalwl ester*' (I) of l,P-discyl-z-glycero-3-phoephorio acid2 (II) are prepared mostly by multistep syntheses3 in nhiah the phoephate eater bonds are created by the reaction of phosphoryl chloride8 with alcohols, or alkyl iodide6 with silver phosphate derivatives. The direct esterification of (II) (scheme 1) provides a short, general and potentially useful route and we have exploited it successfully for the prep8ration of several glycerophoapholipida*. Thie was possible by the choice of 2,4,6-triisopropylbenseneaulphonyl chloride6 (TFS) in the preeenoe of pyridine, ao the condensing agent. Phosphorylation proceeded soothly and little pyrophosphate w8s obtained even in the presence of a two-fold excess of the 8lcohol component. Essentially complete conversions 8r0 obtained and in the three example0 cited hereunder ( chronatographically pure condensation products were isolated in Yl-9syield (based on the phoE#E&tidiC acid).

* The condensation of a phoephatidic acid with glycerol using DCC has been described earlier4. However, a large amount of pyrophosphate is formed as a by-product using this condensing agent4*5.