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Thiosugars. VIII. Preparation of new 4'-thio-L-lyxo pyrimidine nucleoside analogues
J Wirsching1, J Voss, G Adiwidjaja
1Institut für Organische Chemie der Universität Hamburg, Germany.
Nucleosides, Nucleotides & Nucleic Acids
|October 3, 2001
Abstract:
Reaction of 1-O-acetyl-2,3,5-tri-O-benzyl-4-thio-L-lyxofuranose with silylated pyrimidine bases and subsequent deprotection with boron tribromide led to 4'-thio-L-lyxo pyrimidine nucleosides. The 5-bromo-6-methyl derivative was prepared from methyl 2,3,5-tri-O-acetyl-4-thio-L-lyxofuranoside. Deacetylation was performed with sodium methoxide. The anomers were separated by HPLC and their configurations assigned by NMR spectroscopy and X-ray structural analyses. The biological activity of the nucleosides was tested.