Synthesis of N-methyl-D-ribopyranuronamide nucleosides

TETRAHEDRON

卷:64

Article

Yang, Shiqiong¹  Busson, Roger¹  Herdewijn, Piet¹ 

[1] Katholieke Univ Leuven, Rega Inst Med Res, Med Chem Lab, B-3000 Louvain, Belgium

关键词: Ribopyranuronamide;    Nucleosides;    Nucleobase;   

DOI  :  10.1016/j.tet.2008.08.027

来源: Elsevier

【 摘 要 】

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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