Synthesis of a Conformationally Locked AZT Analogue, 3′‐Azido‐3′‐deoxy‐2′‐O,4′‐C‐methylene‐5‐methyluridine

Abstract A bicyclic 3′-azido-3′-deoxythymidine (AZT) analogue with a locked N-conformation, 3′-azido-3′-deoxy-2′- O ,4′- C -methylene-5-methyluridine ( 1a ), and its 3′-amino derivative, 3′-amino-3′-deoxy-2′- O ,4′- C -methylene-5-methyluridine ( 1b ), were successfully synthesized from D-glucose. The conformation of 1a was also discussed by means of 1 H NMR measurements and a molecular modeling (PM3) study.