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Paper | Regular issue | Vol 29, No. 11, 1989, pp.2193-2197
Published online, 1st January, 1970
DOI: 10.3987/COM-89-5160
Facile Synthesis of Pyrrolo[2,3-d]pyrimidine and Pyrrolo[3,2-c]pyridine 2’,3’-Dideoxyribonucleosides via Nucleobase Anion Glycosylation with 2,3-Dideoxy-D-glycero-pentofuranosyl Chloride

F. Seela,* W. Bourgeois, H. -P. Muth, and H. Rosemeyer

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

Abstract

A facile synthesis of pyrrolo[2,3-d]pyrimidine and pyrrolo[3,2-c]pyridine 2’,3’-dideoxyribonucleosides employing a nucleobase anion and 2,3-dideoxy-D-glycero-pentofuranosyl chloride is described. The synthetic route allows large scale preparation of 2’,3’-dideoxytubercidin, 3,7-dideaza-2’,3’-dideoxyadenosine and related basemodified 2’,3’-dideoxyribonucleosides not accessible by conventional glycosylation techniques.