Synthesis and Reactions of Some Glycosylamine Derivatives of 6-Azauracil Nucleosides |
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| Authors: | Najim A Al-Masoudi Ali A Al-Atoom |
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| Institution: | Department of Chemistry , College of Science University of Basrah , Basrah, Iraq |
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| Abstract: | Abstract Reaction of the silylated 6-azauracil (2) with 2-acetamido-1,3,4,6-tetra-O-acetyl-2-deoxy-D-glucose (3) gave 1-(2-acetamido-3,4,6-tri-O-acetyl-2-deoxy-ß-D-glucopyranosyl)-6-azauracil (4), which gave the free nucleoside 5 on deblocking. Acetalation of 5 gave the monoacetal 6 which was oxidized into the ketone 7. Reduction of 7 gave the allo-nucleoside 9 which on hydrolysis afforded the free nucleoside 10. Alternatively, compound 10 was obtained from mesylation of 6 to give 8 followed by subsequent acetolysis and hydrolysis. |
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