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Synthesis 1991; 1991(4): 313-317
DOI: 10.1055/s-1991-26454
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Synthesis of 2′-Azido, 2,2′-Anhydro and 2′,5′-Anhydro Nucleosides with Potential Anti-HIV Activity

Ahmed E. -S. Abdel-Megied* , Erik B. Pedersen, Carsten M. Nielsen
  • *Department of Chemistry, Odense University, Campusvej 55, DK-5230 Odense M, Denmark
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Publication Date:
29 April 2002 (online)

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Reaction of methyl 2-bromo-2,3-dideoxy-5-O-(4-methylbenzoyl)-D-erythro-pentofuranoside (7) with silylated uracils 9 using trimethylsilyl triflate as catalyst afforded the corresponding 2′-bromonucleosides 10. 2,3-Didehydro sugar 8 was prepared by heating 7 with sodium azide in dimethylformamide. 2,2′-Anhydro nucleosides 1 were prepared by treating the nucleosides 10 with sodium methoxide at room temperature. 1-(2-Azido-2,3-dideoxy-β-D-threo-pentofuranosyl)thymine (15) and its α-anomer (16) were prepared by treating 10c with sodium azide and subsequently methanolic ammonia. Treatment of 1-(2-bromo-2,3-dideoxy-α-D-erythro-pentofuranosyl)thymine (11 c) with excess of sodium methoxide under reflux gave the corresponding 2′,5'′anhydro nucleoside 17.

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