Lc. Hwang et al., SYNTHESIS AND STRUCTURE ASSIGNMENT OF 1-(2-ACETOXYETHOXY) METHYL-DERIVATIVES OF 5-CHLORO-6-AZAURACIL AND 5-BROMO-6-AZAISOCYTOSINE, Nucleosides & nucleotides, 13(10), 1994, pp. 2185-2193
1-[(2-Acetoxyethoxy)methyl]-5-chloro-6-azauracil has been prepared and
its unambiguous assignment of H-1 and C-13 peaks through the H-1-C-13
heteronuclear correlation (HETCOR) NMR experiments is described. The
isosteric 1-[(2- acetoxyethoxy)methyl]-5-bromo-6-azaisocytosine has al
so been synthesized. The X-Ray crystallographic analysis reveals unamb
iguously the site of glycosylation at N-1 Deacetylation of both acyclo
nucleosides provided 5-chloro-1-[(2-hydroxyethoxy)methyl]6-azauracil a
nd bromo-1-[(2-hydroxyethoxy)methyl]-6-azaisocytosine respectively. Th
eir structures have been well established by the NMR spectra and the e
lemental analyses.