Synthesis of sn-glycero-1-phosphocholine.

The preparation of sn-glycero-1-phosphocholine is described. 2,3-O-Isopropylidene-sn-glycerol is condensed first with the 1,2-dimethylethenylene phosphorochloridate in the presence of triethylamine to yield the cyclic phosphotriester derivative. Choline p-toluenesulfonate, as the second alcohol, is condensed with this intermediate to yield the phosphotriester bearing the 1-methyl-acetonyl blocking group. This is removed under basic conditions to afford the 2,3-O-isopropylidene-sn-glycerol-1-phosphocholine in 57% yield following silicic acid column chromatography. The acetone blocking group is then removed with aqueous HCl (pH 2.3) to give pure sn-glycero-1-phosphocholine.