J. Iran. Chem. Soc., Vol. 7, No. 3 September 2010, pp.597~602.

Current location: JICS Archive > Vol. 7 > No. 3 > Articles : 5

Design and Synthesis of Novel Dinucleotide Analogs

F. Valiyeva,c,*, V. Abbasovc, H.J. Liua,b and F.Y. Tsaid

aInstitute of Chemistry, Academia Sinica, Taipei 115, Taiwan
bDepartment of Chemistry, National Tsing Hua University, Hsinchu 300, Taiwan
cInstitute of Petrochemical Processes of Azerbaijan NAS, Baku, Azerbaijan
dCenter for General Education, Chang Gung University, Tao-Tuan 333, Taiwan

Syntheses of dinucleotide analogs, (S,R) cis-(4-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-dioxolan-2-yl)methyl (2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl hydrogen phosphate (5a) and (S,R) cis-(5-((4-amino-2-oxopyrimidin-1(2H)-yl)methyl)-1,3-oxathiolan-2-yl)methyl (2R,3R,5R)-2-(hydroxymethyl)-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-tetrahydrofuran-3-yl hydrogen phosphate (5b), were accomplished by the use of a new strategy. The use of phenyldichlorophosphate (Method A) as the coupling reagent was shown to possess superiority relative to the reported use of di(1H-benzo[d][1,2,3]triazol-1-yl)phenyl phosphonate (Method B).

Keywords: Nucleosides, Dinucleotides, Antivirals, Anti-HIV, Phosphorotriesters

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