Synthesis of 6,6′-Cyclo-5′,6′-dideoxy-1-(β-D-allofuranosyl)cytosine and Related Nucleosides (Nucleosides Nucleotides LXXVIII)

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  • Nucleosides and nucleotides. LXXXVIII. Synthesis of 6,6'-cyclo-5',6'-dideoxy-1-(.BETA.-D-allofuranosyl)cytosine and related nucleosides.

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A new synthetic route to 6, 6'-cyclo-5', 6'-dideoxy-1-(β-D-allofuranosyl)-uracil, -cytosine, and -4-thiouracil is described. The method involves a base-catalyzed condensation of 2, 4-dimethoxy-6-methylpyrimidine and 1-O-methyl-2, 3-O-isopropylidene-β-D-ribopentofuranosyldialdehyde, followed by an intramolecular glycosylation, and derivatization of the base moiety. The relationship of the sign of the circular dichroism (CD) spectra of carbon-bridged cyclopyrimidine nucleosides to the glycosyl torsion angle is discussed.

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