Synthesis of a plasmenylethanolamine
Abstract A concise synthesis of a plasmenylethanolamine (PlsEtn-[16:0/18:1 n-9]), known as antioxidative phospholipids commonly found in cell membranes, has been achieved from an optically active known diol through eight steps. The key transformations for the synthesis of PlsEtn-[16:0/18:1 n-9] are, (1) regio- and Z-selective vinyl ether formation via alkylation of a lithioalkoxy allyl intermediate with an alkyl iodide, and (2) a one-pot phosphite esterification–oxidation sequence to construct the ethanolamine phosphonate moiety in the presence of the vinyl ether functionality. The piperidine salt of synthetic PlsEtn-[16:0/18:1 n-9] was desalinated through reversed-phase HPLC purification.
A Reversed-phase HPLC Study of the Complexation of Benzene Derivatives Guest Molecules with 5,17-bis(N-Tolyliminomethyl)-25,27-dipropoxycalix[4]arene in Acetonitrile–Water Solution