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Communication | Regular issue | Vol 36, No. 3, 1993, pp.421-425
Published online, 1st January, 1970
DOI: 10.3987/COM-92-6175
Synthetic Approaches to New Regioisomers of AZT and AZU

Vasu Nair* and David F. Purdy

*Department of Chemistry, The University of Iowa, Iowa City, Iowa 52242, U.S.A.

Abstract

Approaches to 1,4-anhydro-3-α-azido-2,3-dideoxy-2-β-[3,4-dihydro-2,4-dioxo-5-methyl-1(2H)-pyrimidinyl]-D-arabinitol and 1,4-anhydro-3-α-azido-2,3-dideoxy-2-β-[3,4-dihydro-2,4-dioxo-1(2H)-pyrimidinyl]-D-arabinitol, conceptually new hydrolytically stable, optically active analogs of 3’-α-azido-3’-deoxythymidine (AZT) have been developed. These are among the first examples of regioisomeric analogs of AZT. The key synthetic steps and key intermediates are described. The generality aspects of the approaches are addressed.