Collect. Czech. Chem. Commun. 2006, 71, 956-977

Pyrrolo[2,3-d]pyrimidine β-L-Nucleosides Containing 7-Deazaadenine, 2-Amino-7-deazaadenine, 7-Deazaguanine, 7-Deazaisoguanine, and 7-Deazaxanthine

Frank Seelaa,b,* and Xiaohua Penga,b

a Laboratorium für Organische und Bioorganische Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany
b Laboratory of Bioorganic Chemistry and Chemical Biology, Center for Nanotechnology, Heisenbergstrasse 11, D-48149 Münster, Germany


The synthesis and properties of 7-deazapurine β-L-nucleosides are described. The stereoselective glycosylation of the anions of 2-amino-6-chloro-7-deazapurines 9a, 9b or 6-chloro-7-deazapurines 13a, 13d with 3,5-di-O-(4-methylbenzoyl)-2-deoxy-α-L-erythro-pentofuranosyl chloride (8) furnished the β-L-2'-deoxyribonucleosides 1-4. The synthesis of β-L-ribonucleosides 5-7 used the Silyl-Hilbert-Johnson reaction (TMSOTf/BSA/MeCN) performed under Vorbrüggen conditions for the glycosylation of 7-halogenated 6-chloro-2-pivalamido-7-deazapurines 17b-17d with 1-O-acetyl-2,3,5-tri-O-benzoyl-L-ribofuranose (16). Single-crystal X-ray analyses were performed and CD spectra were measured to assign the configuration. The antiviral activity against selected DNA and RNA viruses is reported.

Keywords: Nucleosides; Purines; 7-Deazapurines; Pyrrolo[2,3-d]pyrimidines; β-L-2'-Deoxyribonucleosides; β-L-Ribonucleosides; Nucleobase anion glycosylation; NMR spectroscopy; CD spectroscopy; Antiviral activity.

References: 33 live references.