PHOSPHITE TRIESTER AND H-PHOSPHONATE APPROACHES IN THE SYNTHESIS OF PHOSPHOLIPIDS

Presented review is focused on phosphoramidite and H-phosphonate approaches employed for the construction of phosphodiester fragment of phospholipids and other natural phosphodiesters and their analogs at phosphorus. The principles of both methods are considered in detail. The merits and potentialities of the methods enlisted the literature covering not only the synthesis of phospholipids, but the synthesis of oligonucleotides, phosphorylated carbohydrates and amino acids as well are discussed. Comprehensive data on phosphitylating and condensing agents are summarized. Special consideration is given to the approaches towards the preparing of the phosphoramidites and monoesters of phosphoric acid (H-phosphonate monoesters), the procedures of the activation and condensation of these initial monomers with nucleofiles, the means of the oxidation of phosphites to phosphates and the ways for the synthesis of P-chiral and other analogs at phosphorus. Particular emphasis is placed upon the application of the latest modifications of phosphoramidite and H-phosphonate approaches to the synthesis of phospholipids including glycero-, sphingo- and glycophospholipids.