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.
D004148:Dioxolanes; D005021:Ethylamines; D005997:Glycerylphosphorylcholine / Q000138:chemical synthesis*; D007202:Indicators and Reagents
D004148:Dioxolanes; D005021:Ethylamines; D007202:Indicators and Reagents; C024356:2,2-dimethyl-1,3-dioxolane-4-methanol; D005997:Glycerylphosphorylcholine; C016162:triethylamine