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Communication | Regular issue | Vol 34, No. 2, 1992, pp.229-236
Published online, 1st January, 1970
DOI: 10.3987/COM-91-9515
7-Deazaguanosine: Phosphoramidite and Phosphonate Building Blocks for Solid-Phase Oligoribonucleotide Synthesis

Frank Seela* and Karin Mersmann

*Laboratorium für Organische and Bioorganische Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Barbarastr. 7, D-4500 Osnabrück, Germany


The synthesis of oligoribonucleotide building blocks (phosphonates and phosphoramidites) of 7-deazaguanosine (2-amino-7-(β-D-ribofuranosyl)-7H-pyrrolo[2,3-d]pyrimidin-4(3H)-one, 1) is described. Silylation of the 2'-hydroxy group of 7-deaza-N2-isobutyryl-5'-O-(4-monomethoxytrityl)guanosine (5) was studied with regard to the 2'-selectivity. Best results were obtained with triisopropylsilyl chloride/AgNO3. The 2'-O-protected intermediates (6a and 6b) were converted into the phosphonates (3a, b) or methylphosphoramidites (4a, b), which were successfully used for solid-phase oligoribonucleotide synthesis of (c7G-C)3 (9).