The synthesis of some 5-alkyl (cycloalkyl)-substituted 2'-deoxy-4'-thiouridines

Article abstract of DOI:10.1080/07328319608002375

The silylated pyrimidine bases IIa-d were condensed with the benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-D-erythro-pentofuranoside III in acetonitrile under activation by N-iodosuccinimide, giving ca 1.5:1/α:β anomeric mixtures of the blocked nucleosides IVa-d and Va-d. in yields of 55-88%. After the separation on a silica column the pure anomers were deprotected by BCl₃ or TiCl₄, providing the free nucleosides VIa-d and VIIa,c,d in moderate to good overall yields. The β- or α-anomeric configuration, anti-glycosidic conformation and prevailing C2'-endo(S) thiosugar pucker in the synthesized compounds were established by the combined use of the ¹H, ¹³C NMR and X-ray crystallography.

Full text of DOI:10.1080/07328319608002375

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The Synthesis of Some 5-Alkyl
(Cycloalkyl)-Substituted 2′ -Deoxy-4′-
Thiouridines
I. Basnak a , M. Sun a , P. L. Coe a & R. T. Walker a
a School of Chemistry, The University of Birmingham ,
Birmingham, B15 2TT, UK
Published online: 21 Aug 2006.
To cite this article: I. Basnak , M. Sun , P. L. Coe & R. T. Walker (1996) The Synthesis of Some 5-
Alkyl (Cycloalkyl)-Substituted 2′ -Deoxy-4′-Thiouridines, Nucleosides and Nucleotides, 15:1-3,
121-134
To link to this article: http://dx.doi.org/10.1080/07328319608002375
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