The syntheses of various fluorocarbon/Ruorocarbon and fluorocarbon/hydrocarbon rac-l,2-and 1,3-di-0-alk(en)ylglycerophosphocholines and rac-l,2-di-O-alkylglycerophosphoethanolamines (see Fig. 2), which may be used as components for drug-carrier and delivery systems, are described together with some results concerning their biological tolerance. They were obtained by phosphorylation of perfluoroalkylated ruc-di-0 -alk(en)ylglycerols using POCI,, then condensation with choline tosylate or N-Boc-ethanolamine (2-[(tert -butoxy)carbonylaminolethanol) followed by Boc-deprotection (Schemes 6-8). The flnorocarbon/fluorocarbon 1,2-di-0 -alkylglycerols were prepared by 0-alkylation of ruc-1-0-benzylglycerol using perfluoroalkylated mesylates, then hydrogenolysis for benzyl deprotection (Scheme 1 ). The two different hydrophobic chains in the mixed fluorocarbon/ fluorocarbon and fluorocarbon/hydrocarbon 1,2-di-O-alk(en)ylglycerols were introduced starting from 1,2-0 -isopropylidene-then 0 -trityl-protected glycerols or from 1,3-0 -benzylidene-glycerol (Schemes 3 and 4). The perfluoroalkylated 0-alkenylglycerols were obtained by 0-alkylation of a glycerol derivative using an o-unsaturated alkenyl reagent, the perfluoroalkyl segment being connected onto the double bond in a subsequent step (Schemes 1 and 3 ) . The perfluoroalkylated symmetrical and mixed 1,3-di-0 -alkylglycerols were synthesized by displacement of the C1-atom in epichlorohydrin by perfluoroalkylated alcohols, then catalytic (SnCI.,) opening of the oxirane ring of the resulting alkyl glycidyl ethers in neat alcohols (Scheme 5 ) . When injected intravenously into mice, acute maximum tolerated doses higher than 1500 and 2000 mg/kg body weight were observed for the fluorinated glycerophosphocholines, indicating a very promising in vivo tolerance.
