175470-91-4Relevant academic research and scientific papers
The synthesis of some 5-alkyl (cycloalkyl)-substituted 2'-deoxy-4'-thiouridines
Basnak,Sun,Coe,Walker
, p. 121 - 134 (2007/10/03)
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.
