Design and Synthesis of Novel Dinucleotide Analogs

F. Valiyev^a,c,, V. Abbasov^c, H.J. Liu^a,b and F.Y. Tsai^d*

^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

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

F. Valiyev^a,c,, V. Abbasov^c, H.J. Liu^a,b and F.Y. Tsai^d*

^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