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Synthesis 1991; 1991(6): 451-454
DOI: 10.1055/s-1991-26490
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Selective Deformylation of an α,β-Unsaturated Sugar Aldehyde in a Very Short Synthesis of 3′-Azido-3′-deoxythymidine (AZT) and its Stereoisomers

Jesper Wengel* , Erik B. Pedersen
  • *Department of Chemistry, Odense University, DK-5230 Odense M, Denmark
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Publication Date:
29 April 2002 (online)

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(2E,4S)-5-Acetoxy-4-formyloxy-2-pentenal (2) prepared in one step from tri-O-acetyl-D-glucal was selectively deformylated to give the α,β-unsaturated aldehyde 3 with an unprotected hydroxy group at C-4. Michael-type addition reaction of hydrazoic acid to 3 followed by acylation at C-1 gave a 1:1 mixture of the erythro- and threo-isomers of 5-O-acetyl-3-azido-1 -O-(4-biphenylcarbonyl)-2,3-dideoxypentofuranoses 4 and 5. They were used as substrates for nucleoside coupling with silylated thymine to give all four D-isomers of 3′-azido-3′-deoxythymidine 6-9.