Journal
TETRAHEDRON
Volume 64, Issue 43, Pages 10062-10067Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2008.08.027
Keywords
Ribopyranuronamide; Nucleosides; Nucleobase
Categories
Funding
- Chinese Scholarship Council
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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.
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