Collect. Czech. Chem. Commun. 1980, 45, 2550-2557

Synthesis of dinucleoside phosphates containing 5'-O-bonded 1-(6-deoxy-β-D-allofuranosyl)uracil and 1-(6-deoxy-α-L-talofuranosyl)uracil

Nella Sh. Padyukovaa and Jiří Smrtb

a Institute of Molecular Biology, Academy of Sciences of the USSR, Moscow, U.S.S.R.
b Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6, Czechoslovakia


1-O-Acetyl-2,3,5-tri-O-benzoyl-6-deoxy-L-talofuranose (IV) affords by the reaction with silylated uracil in the presence of stannic chloride, followed by the action of methanolic ammonia, 1-(6-deoxy-α-L-talofuranosyl)uracil (Vb). 1-(6-Deoxy-β-D-allofuranosyl)uracil (IIb) and/or the compound Vb reacts with ethyl orthoformate in the presence of hydrogen chloride under the formation of 2',3'-O-ethoxymethylene derivatives III or VI which afford, by the reaction with pyridinium salts of 2'-O-tetrahydropyranyl-5'-O-acetyl-(N-acetyl)ribonucleoside 3'-phosphates VIIa-VIId in the presence of N,N'-dicyclohexylcarbodiimide and the removal of protecting groups, ribonucleosid-3'-phosphorylyl-(3' → 5')-1-(6-deoxy-β-D-allofuranosyl)uracils IXa-IXd and/or ribonucleosid-3'-phosphorylyl-(3' → 5')-1-(6-deoxy-α-L-talofuranosyl)uracils Xa-Xd.