Thiosugars. X. Novel nucleoside analogues derived from 4-thio-L-lyxofuranose.
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 anti-virically inhibitory at 250 microM.
Wirsching
Jörn
J
Institut für Organische Chemie der Universität Hamburg, Hamburg, Germany.
Voss
Jürgen
J
Giesler
Anja
A
Kopf
Jürgen
J
Adiwidjaja
Gunadi
G
Balzarini
Jan
J
De Clercq
Erik
E
D000998:Antiviral Agents / Q000737:chemistry / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008968:Molecular Conformation; D015394:Molecular Structure; D009691:Nucleic Acid Denaturation; D009705:Nucleosides / Q000737:chemistry* / Q000494:pharmacology; D010429:Pentoses / Q000737:chemistry*; D011522:Protons; D013876:Thiophenes / Q000737:chemistry*; D014961:X-Ray Diffraction
C487121:1-O-acetyl-2,3,5-tri-O-benzyl-4-thiolyxose; D000998:Antiviral Agents; D009705:Nucleosides; D010429:Pentoses; D011522:Protons; D013876:Thiophenes