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■ 1-Deaza-2’-deoxyadenosine: Phosphonate and Phosphoramidite Building Blocks for Solid-Phase Oligonucleotide Synthesis

Frank Seela* and Thomas Wenzel

*Laboratorium für Organische und Bioorganische Chemie, Institut für Chemie, Universität Osnabrück, Barbarastr. 7, D-4500 Osnabrück, Germany

Abstract

The synthesis of the 3’-[(2-cyanoethyl)diisopropylphosphoramidite] (3b) and the 3’-phosphonate (3a) of 1-deaza-2’-deoxyadenosine (1b) is described. For this purpose compound 1b was protected at the 6-amino group with a benzoyl residue. Ensuing 4,4’-dimehoxytritylation of 1b and phosphitylation afforded the P(III) derivatives (3a) and (3b). They were successfully employed in solid-phase oligodeoxyribonucleotide synthesis of d(c¹A-c¹A-c¹ A-A-A-A) (6). ¹³C-Nmr and ¹⁵N-nmr spectra of the compounds (1-5) are discussed.