1-DEAZA-2'-DEOXYADENOSINE - PHOSPHONATE AND PHOSPHORAMIDITE BUILDING-BLOCKS FOR SOLID-PHASE OLIGONUCLEOTIDE SYNTHESIS

Autor(en): SEELA, F
WENZEL, T
Stichwörter: Chemistry; Chemistry, Organic; DEOXYNUCLEOSIDES; DNA; RIBONUCLEOSIDES
Erscheinungsdatum: 1993
Herausgeber: PERGAMON-ELSEVIER SCIENCE LTD
Journal: HETEROCYCLES
Volumen: 36
Ausgabe: 2
Startseite: 237
Seitenende: 242
Zusammenfassung: 
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 lb was protected at the 6-amino group with a benzoyl residue. Ensuing 4,4'-dimethoxytritylation of lb and phosphitylation afforded the P(III) derivatives(3a) and (3b). They were successfully employed in solid-phase oligodeoxyribonucleotide synthesis of d(c1A-c1A-c1A-A-A-A) (6). C-13-Nmr and N-15-nmr spectra of the compounds (1-5) are discussed.
ISSN: 03855414
DOI: 10.3987/COM-92-6214

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