Collect. Czech. Chem. Commun. 1982, 47, 2157-2169

3'-O-Formyl-(N-acyl)-2'-deoxyribonucleosides as building units in the synthesis of oligodeoxyribonucleotides

Jiří Smrt

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


5'-O-Dimethoxytrityl-(N-acyl)-2'-deoxyribonucleosides afford 3'-O-formyl-(N-acyl)-2'-deoxyribonucleosides Ia-Id by the action of formic acetic anhydride followed by the action of 80% aqueous acetic acid. The formyl group is removed from Ia-Id by treatment with 1 mol l-1 triethylamine 3'-O-Formyl-2'-deoxythymidine (Ia) gives 3'-O-dimethoxytrityl-2'-deoxythymidine (V) by subsequent treatment with acetic anhydride, triethylamine, dimethoxytrityl chloride and methanolic ammonia. The use of compounds I for the synthesis of d-GGAGG (XIX) and d-T16 (XXXII) is described. Systems for thin-layer chromatography of 5'-O-dimethyltrityl-oligodeoxyribonucleotides on silica gel are described.