Synthesis 1995; 1995(3): 265-270
DOI: 10.1055/s-1995-3892
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2’-Deoxypuromycin: Synthesis and Antiviral Evaluation

Mohammed S. Motawia, Morten Meldal, Mamdouh Sofan, Paul Stein, Erik B. Pedersen* , Claus Nielsen
  • *Department of Chemistry, Odense University, Campusvej 55, DK-5230 Odense M, Denmark
Further Information

Publication History

Publication Date:
31 December 2000 (online)

A new synthesis of 2’-deoxypuromycin (18) as well as its α-anomer 17 is described. Reaction of 1,5-di-O-acetyl-2,3-dideoxy-3-phthalimido-D-erythro-pentofuranose (3) with silylated 6-dimethylaminopurine using trimethylsilyl trifluoromethanesulfonate as catalyst afforded the α and β nucleosides 7 and 12 in 15 and 25% yield, respectively. After deblocking of both amino and hydroxy groups with methylamine in ethanol, the nucleosides were condensed with Fmoc-4-O-methyl-L-tyrosine and subsequently deprotected to give the target compounds 17 and 18. Compound 3 is converted into its glycosyl bromide 4 in quantitative yield on treatment with trimethylsilyl bromide, and reacted with the sodium salt of 6-dimethylaminopurine to give the corresponding protected N-7 and N-9 α glycosyl nucleosides 7 and 8 in 34 and 39% yield, respectively. The 2’-deoxypuromycin is inactive against HIV-1 in MT-4 cells.