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Modified nucleosides part 8 nucleosides of pento furan uronic acids

Modified nucleosides part 8 nucleosides of pento furan uronic acids

Bioorganicheskaya Khimiya 2(5): 621-626

The syntheses and transformations of 1-(methyl 2-O-acetyl-3-O-p-toluenesulfonyl-.beta.-D-xylofuranosyluronate)uracil (II), -N(4)-benzoylcytosine (IV) and N(9)-(methyl 2-O-acetyl-3-O-p-toluenesulfonyl-.beta.-D-xylofuranosyluronate)-N(6)-benzoyladenine (V) were studied. Unsaturated nucleosides 1-(methyl 2-O-acetyl-3-deoxy-.beta.-D-glyceropent-3-enofuranosyluronate)uracil (VI), 1-(3-deoxy-.beta.-D-glyceropent-3-enofuranosyluronamide)uracil and N(9)-(3-deoxy-.beta.-D-glyceropent-3-enofuranosyluronamide)adenine, as well as 1-(O2,2-cyclo-.beta.-D-arabinofuranosyluronamide)uracil and 1-(.beta.-D-arabinofuranosyluronamide)uracil and -cytosine were obtained upon the action of various bases on the nucleosides (II), (IV) and (V). Catalytic hydrogenation of the nucleoside (VI) afforded 1-(methyl 3-deoxy-.beta.-D-erythropentofuranosyluronate)uracil and 1-(methyl 3-deoxy-.alpha.-L-threopentofuranosyluronate)uracil.

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