Synthesis and ¹H and ¹³C NMR Spectral Characteristics of 8-Bromo-2′,3′-Dideoxyguanosine and 8-Bromo-2′,3′-Dideoxyinosine¹

1. For preliminary communication see: Zeidler, J.; Golankiewicz, B. Collect. Czech. Chem. Commun., Special Issue1993, 58, 71.

Abstract

Reaction of 2′,3′-dideoxyguanosine 1a as 5′-O-tert-butyldimethylsilyl derivative 1b and 2′,3′-dideoxyinosine 2a with bromine in acetate buffer conducted in heterogeneous medium afforded 8-bromo-2′,3′-dideoxyguanosine 3a (44% after deprotection) and 8-bromo-2′,3′-dideoxyinosine 4a (12%) respectively. The change of conformational preferences anti → syn on 8-bromo substitution of 2′,3′-dideoxynucleosides is reflected in the ¹H and ¹³C NMR spectra by characteristic shifts of H-2′, H-3′, C-2′ and C-3′ signals.

1. For preliminary communication see: Zeidler, J.; Golankiewicz, B. Collect. Czech. Chem. Commun., Special Issue 1993, 58, 71.

Notes

1. For preliminary communication see: Zeidler, J.; Golankiewicz, B. Collect. Czech. Chem. Commun., Special Issue 1993, 58, 71.