Synthesis 1991; 1991(3): 239-240
DOI: 10.1055/s-1991-26434
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An Efficient Synthesis of 3′-Azido-3′-deoxythymidine (AZT)

Stanislas Czernecki* , Jean-Marc Valéry
  • *Laboratoire de Chimie des Glucides, Université Pierre et Marie Curie, T74, E6, 4, Place Jussieu F-75005 Paris, France
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17. September 2002 (online)

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.