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Synthesis 1996; 1996(2): 237-241
DOI: 10.1055/s-1996-4187
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Synthesis of S 2-Alkyl-2-thiouridines

Adel A.-H. Abdel-Rahman, Magdy A. Zahran, Ahmed E.-S. Abdel-Megied, Erik B. Pedersen* , Claus Nielsen
  • *Department of Chemistry, Odense University, Campusvej 55, DK-5230 Odense M, Denmark, Fax +4566158780; E-mail EBP@OUKEMI.OU.DK
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Publication History

Publication Date:
31 December 2000 (online)

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5-Substituted S 2-alkyl-2-thiouracils 1a-i were treated with 1,1,1,3,3,3-hexamethyldisilazane and ammonium sulfate at reflux temperature and condensed with 1,2,3,5-tetra-O-acetyl-β-D-ribufuranose in acetonitrile using trimethylsilyl trifluoromethanesulfonate as a catalyst to afford the corresponding protected nucleosides 2a-i which were deprotected with saturated ammonia in methanol. When the nucleobase was substituted with ethoxycarbonyl or cyano groups in the 5-position or was unsubstituted, the deprotection reaction of the nucleoside also resulted in replacement of the methylthio group. This was not observed with 5-alkyl and 5-methoxy substituents.

HIV - nucleoside synthesis - O 2-methyl - 2-thiouridines - S 2-alkyl

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