Synthesis of derivatives of C-nucleoside analogues using 'push-pull' functionalized monosaccharides.
7-Deoxy-1,2:3,4-di-O-isopropylidene-alpha-D-galacto-heptopyranos-6-ulose (1) reacted with carbon disulphide and methyl iodide in the presence of a base to furnish 7,8-dideoxy-1,2:3,4-di-O-isopropylidene-8,8-[bis(methylthio)]-alpha-D-galacto-oct-7-enopyranos-6-ulose (2). This 'push-pull' activated unsaturated monosaccharide underwent a ring closure reaction with hydrazine hydrate to give the 'inversed' C-nucleoside analogue 3. Compound 1 and malononitrile yielded the 7-cyano-6,7-dideoxy-1,2:3,4-di-O-isopropylidene-6-methyl-alpha-D-galacto-oct-6-enopyranurononitrile (4). Treatment of 4 with carbon disulphide and methyl iodide in the presence of a base afforded the sugar 'push-pull' butadiene 5 which was transformed into the pyridine nucleoside analogue 6.
Michalik
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D
Fachbereich Chemie, Universität Rostock, D-18051 Rostock, Germany.
Feist
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H
Peseke
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D000970:Antineoplastic Agents / Q000138:chemical synthesis; D000998:Antiviral Agents / Q000138:chemical synthesis; D009005:Monosaccharides / Q000138:chemical synthesis*; D009705:Nucleosides / Q000138:chemical synthesis*; D011725:Pyridines / Q000138:chemical synthesis
D000970:Antineoplastic Agents; D000998:Antiviral Agents; D009005:Monosaccharides; D009705:Nucleosides; D011725:Pyridines