Thiosugars. X. Novel Nucleoside Analogues Derived from 4-Thio-<scp>L</scp>-lyxofuranose
作者:Jörn Wirsching、Jürgen Voss、Anja Giesler、Jürgen Kopf、Gunadi Adiwidjaja、Jan Balzarini、Erik De Clercq
DOI:10.1081/ncn-120025236
日期:2003.10.1
1-O-Acetyl-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose 1 was transformed into O-benzyl- and O-acetyl-protected 1-(4-thio-L-lyxofuranosyl) nucleoside derivatives by use of the TMSOTf method. Debenzylation with boron tribromide or deacetylation with sodium methoxide yielded the corresponding pyrimidine (7-11, 17, 18, 26 and 27) and purine (29 and 34) nucleoside analogues. The anomeric configurations were determined by NMR spectroscopy and, in the case of the 5-halo- (7-9) and nitrouridine derivative 11 and the 6-methylcytidine derivative 27, by X-ray structural analyses. - The unprotected nucleosides were not antivirically inhibitory at 250 muM.