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Synthesis and Structure Assignment of 1-(2-Acetoxyethoxy)methyl Derivatives of 5-Chloro-6-azauracil and 5-Bromo-6-azaisocytosine |
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| Authors: | L.-C. Hwang D.-C. Wei M.-C. Cheng Y. Wang C.-C. Tzeng |
| Affiliation: | 1. School of Chemistry, Kaohsiung Medical College , Kaohsiung City, 807, Taiwan, R. O. C.;2. Department of Chemistry , National Taiwan University , Taipei City, 107, R. O. C.;3. Department of Chemistry , National Taiwan University , Taipei City, 107, R. O. C. |
| Abstract: | Abstract 1-[(2-Acetoxyethoxy)methyl]-5-chloro-6-azauracil has been prepared and its unambiguous assignment of 1H and 13C peaks through the 1H-13C heteronuclear correlation (HETCOR) NMR experiments is described. The isosteric 1-[(2-acetoxyethoxy)methyl]-5-bromo-6-azaisocytosine has also been synthesized. The X-Ray crystallographic analysis reveals unambiguously the site of glycosylation at N1. Deacetylation of both acyclonucleosides provided 5-chloro-1-[(2-hydroxyethoxy)methyl]-6-azauracil and 5-bromo-1-[(2-hydroxyethoxy)methyl]-6-azaisocytosine respectively. Their structures have been well established by the NMR spectra and the elemental analyses. |
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