Synthesis and Properties of 3′-Deoxypsiconucleosides: Anomeric 1-(3-Deoxy-D-erythro-2-hexulofuranosyl) thymines and 9-(3-Deoxy-D-erythro-2-hexulofuranosyl)adenines

Alex Azhayev; Andrei Guzaev; Jari Hovinen; Jorma Mattinen; Reijo Sillanpää; Harri Lönnberg

doi:10.1055/s-1994-25485

Synthesis 1994; 1994(4): 396-400
DOI: 10.1055/s-1994-25485

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Synthesis and Properties of 3′-Deoxypsiconucleosides: Anomeric 1-(3-Deoxy-D-erythro-2-hexulofuranosyl) thymines and 9-(3-Deoxy-D-erythro-2-hexulofuranosyl)adenines

Alex Azhayev^* , Andrei Guzaev, Jari Hovinen, Jorma Mattinen, Reijo Sillanpää, Harri Lönnberg

^*Department of Chemistry, University of Turku, FIN-20500 Turku, Finland

Abstract

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Anomeric 1-(3-deoxy-D-erythro-2-hexulofuranosyl)thymines and 9-(3-deoxy-D-erythro-2-hexulofuranosyl)adenines were prepared by tin(IV) chloride catalyzed N-glycosylation of trimethylsilylated thymine and N ⁶-benzoyladenine with methyl 3-deoxy-D-erythro-2-hexulofuranoside triacetate or tribenzoate, respectively. These O-glycosides used as starting materials were obtained by deoxygenation of 1,2:4,5-di-O-isopropylidene-β-D-fructopyranose and subsequent acid-catalyzed methanolysis of the resulting 3-deoxy derivative. The anomeric configuration of the nucleosides prepared was assigned by a combination of X-ray crystallography and 2D ¹H NMR spectroscopy. The conformation and hydrolytic stability of these new nucleoside analogous are discussed.

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