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Paper | Regular issue | Vol 29, No. 4, 1989, pp.795-805
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4898
Synthesis of 1,7-Dideaza-2’-deoxyadenosine and Related Pyrrolo[2,3-b]pyridine 2’-Deoxy-β-D-ribonucleosides: Stereoselective Phase-Transfer Glycpsylation via the Nucleobase Anion

F. Seela* and R. Gumbiowski

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

Abstract

The synthesis of 1,7-dideaza-2’-deoxyadenosine (1) and related pyrrolo[2,3-b]pyridine 2’-deoxy-β-D-ribofuranosides is described. Glycosylation of the anions of the pyrrolo[2,3-b]pyridines 5a or 5b with 2-deoxy-3,5-di-O-(p-toluoyl)-α-D-erythro-pentofuranosyl chloride (6) has been carried out under phase-transfer conditions (MeCN, solid KOH, TDA-1, 25°C) and was complete within less than 15 min. The reaction was stereoselective and β-nucleosides were formed exclusively. The position of glycosylation as well as the anomeric configuration were assigned by NOE difference spectroscopy. Compound 1 was extremely stable against acid or base and was not deaminated by adenosine deaminase.