Modification of polyprenol by phosphorylation and acylation

Abstract

Polyprenol isolated from spruce needles was subjected to phosphorylation and acylation. Its phosphorylation with hexaethylphosphorous triamide in dioxane afforded bis(polyprenyl) N,N-diethylphosphoramidite which was hydrolyzed to bis(polyprenyl) phosphonate. The latter can be used in the synthesis of prodrugs. The acylation of polyprenol with aromatic and heterocyclic carboxylic acid chlorides gave the corresponding esters as potential precursors of pharmacologically important compounds. The structure of the isolated compounds was confirmed by 1 H, 31 P, and 13 C NMR and IR spectra.