2'-Deoxypuromycin: Synthesis and antiviral evaluation

M. S. Motawia, M. Meldal, M. Sofan, P. Stein, E. B. Pedersen*, C. Nielsen

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Abstrakt

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-β-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.

OriginalsprogEngelsk
TidsskriftSynthesis
Udgave nummer3
Sider (fra-til)265-270
Antal sider6
ISSN0039-7881
StatusUdgivet - 1. jan. 1995

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