Study of asymmetrically substituted myo-inositols. XXXIX. The synthesis of conjugate of 2',3'-didehydro-3'-dehydroxythymidine with phosphatidylinositol: a new nucleoside phospholipid with potential anti-HIV activity

A partially protected phosphatidylinositol with a free hydroxyl group in the cyclitol moiety was synthesized by phosphorylation of a tetrasubstituted myo-inositol using the H-phosphonate and phosphoamidite methods. The H-phosphonate method was advantageous for the synthesis of selectively protected monophosphoinositide due to a lesser number of stages. Two schemes for the conjugation of 2',3'-didehydro-3'-dehydroxythymidine with phosphatidylinositol using succinic acid as a linker were tested in the synthesis of the target nucleoside phospholipid.