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Keywords:

ribopyranuronamide, nucleosides, nucleobase, adenosine receptors, derivatives, lactams, analogs, ribose, acids, rna, Science & Technology, Physical Sciences, Chemistry, Organic, Chemistry, Ribopyranuronamide, Nucleosides, Nucleobase, ADENOSINE RECEPTORS, DERIVATIVES, LACTAMS, ANALOGS, RIBOSE, ACIDS, RNA, 0304 Medicinal and Biomolecular Chemistry, 0305 Organic Chemistry, Organic Chemistry, 3101 Biochemistry and cell biology, 3404 Medicinal and biomolecular chemistry, 3405 Organic chemistry

Abstract:

The Synthesis of N-methyl-D-ribopyranuronamide nucleosides is described. The key route is the rearrangement of a 1,2-O-isopropylidene protected furanose sugar with a carboxamide function in the 4-position to a ribopyranuronamide ring. The Lewis acid catalyzed condensation of adenine and thymine nucleobases with the per-O-acetylated N-methyl-D-ribopyranuronamide sugar is used to give the target nucleosides as a mixture of the alpha and beta anomers. The mixture was separated and the final Compounds were obtained by deacetylation in basic conditions. (C) 2008 Elsevier Ltd. All rights reserved.