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Communication | Regular issue | Vol 26, No. 7, 1987, pp.1755-1760
Published online, 1st January, 1970
DOI: 10.3987/R-1987-07-1755
2’-Deoxy-3,7-dideazanebularine and 2’-Deoxy-3,7-dideazainosine: Synthesis of Pyrrolo[3,2-c]pyridine β-D-2’-Deoxyribofuranosides by Solid-liquid Phase-transfer Glycosylation

Frank Seela and Werner Bourgeois

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

Abstract

1-(2-Deoxy-β-D-erythro-pentofuranosyl)-1H-pyrrolo-[3,2-c]pyridine (2’-deoxy-3,7-dideazanebularine,1) and 1- (2-deoxy-β-Derythro- pentofuranosy1)-1H-pyrrolo[3,2-c]pyridin-4(5H)-one (2’-deoxy-3,7-dideazainosine, 2a) have been synthesized by regio- and diastereospecific solid-liquid phase-transfer glycosylation. Employing the cryptand TDA-1, solid KOH, and an aprotic solvent the nucleoside 6 was formed in almost quantitative yield. It was converted into compounds 2b or 3b by selective displacement of the 4-chloro group. Compounds 1, 2a, or 3c were obtained after catalytic hydrogenation. The nucleoside 2a is extremely stable under acidic as well as under alkaline conditions. Compound 1 is strongly fluorescent.