1366405-64-2Relevant academic research and scientific papers
Synthesis of (Z)-(2′R)-1-O-(2′-methoxynonadec-10′-enyl)- sn-glycerol, a new analog of bioactive ether lipids
Pemha, René,Pegnyemb, Dieudonné Emmanuel,Mosset, Paul
, p. 2973 - 2983 (2012/06/01)
An unsaturated 2-methoxy-substituted 1-O-alkylglycerol, (Z)-(2′R)-1-O-(2′-methoxynonadec-10′-enyl)-sn-glycerol, a new analog of bioactive ether lipids, was synthesized from oleic acid and 2,3-isopropylidene-sn-glycerol. The two key steps of this synthesis were the conversion of oleyl aldehyde to a monounsaturated epoxide using Matteson's method followed by hydrolytic kinetic resolution and a nucleophilic epoxide opening by 2,3-isopropylidene-sn-glycerol in the presence of potassium tert-butoxide in anhydrous DMF, which appeared to be a good reagent for this purpose. Furthermore, the diol by-product of the HKR process was also easily converted back to the starting epoxide thus almost doubling the amount of target molecule.
