Patent ID: 7807847
Filing Date: 2010-10-05
Classification: C07B,C07C,C07F,Y02P

Abstract:
1. A method of preparing a compound having a glycerolic backbone and at least one oxidized moiety-containing residue attached to the glycerolic backbone via an ether bond, the compound having the general Formula II: wherein: A A R R whereas: X is an alkyl chain having 1-24 carbon atoms; Y is hydrogen; and Z is selected from the group consisting of: with R R providing a first compound having a glycerolic backbone and at least one free hydroxyl group, said first compound having general Formula I: wherein A providing a second compound, said second compound comprising 6-30 carbon atoms, including an unsaturated moiety having at least one unsaturated bond which is capable of being subjected to oxidative cleavage, and at least one leaving group for forming an ether bond with said free hydroxyl group; reacting said first compound and said second compound to thereby obtain a third compound, said third compound having said glycerolic backbone, said A wherein when R collecting said third compound; providing a solution of said third compound in a non-polar solvent, said non- polar solvent being selected such that said third compound is soluble therein whereby impurities formed during said reacting are insoluble therein, to thereby provide a mixture including said solution of said third compound in said non-polar solvent and insoluble impurities; removing said insoluble impurities; and removing said non-polar solvet, to thereby obtain a purified third compound; reacting said purified third compound with an oxidizing agent so as to oxidize said unsaturated moiety to form said Z, to thereby obtain a fourth compound, said fourth compound having said glycerolic backbone and an oxidized moiety-containing residue attached to said glycerolic backbone via an ether bond at position sn-2; and isolating said fourth compound to thereby obtain a purified fourth compound, thereby obtaining the compound having a glycerolic backbone and at least one oxidized moiety-containing residue attached to said glycerolic backbone via an ether bond, said isolating of said third compound and said isolating of said fourth compound each being devoid of column chromatography, wherein when the compound having a glycerolic backbone and at least one oxidized moiety-containing residue attached to the glycerolic backbone further comprises a phosphorous-containing moiety attached to the glycerolic backbone, said phosphorous-containing moiety is a phosphate moiety attached to the glycerolic backbone via a phosphodiester bond, such that R the method further comprises, subsequent to isolating said fourth compound: providing said purified fourth compound having a free hydroxyl group; reacting said purified fourth compound with a reactive phosphorous- containing compound having a second reactive group and a third reactive group, said second reactive group being capable of reacting with said free hydroxyl group, to thereby provide said purified fourth compound having a reactive phosphorous- containing group attached to the glycerolic backbone; and converting said reactive phosphorous-containing group to said phosphorous- containing moiety.