An efficient synthesis of 3'-azido-3'-deoxythymidine (AZT)

Article abstract of DOI:10.1055/s-1991-26434

A very efficient synthesis of 3'-azido-3'-deoxythymidine (4) (AZT) from thymidine is described. The key step is a one-pot transformation of thymidine into 2,3'-anhydro-5'-O-(4-methoxybenzoyl)-thymidine (2) which is isolated by direct crystallization. Further ring opening of 2 with the azide ion and 5'-O-deprotection afforded AZT in 73% overall yield.