Aah. Abdelrahman et Mta. Aal, SYNTHESIS OF (S)-1-(2',3'-DIHYDROXYPROPYL)-2-ALKYLTHIOURACILS AS NEW ANTIVIRAL AGENTS, Die Pharmazie, 53(6), 1998, pp. 377-380
2-Alkylthiouracils 1a-f have been prepared. Nucleoside coupling of 2 w
ith sodium salt of 1a-f gave the corresponding dioxolane derivatives 3
a-f which were treated with 80% acetic acid at reflux temperature to g
ive (S)-1-(2',3'-dihydroxypropyl)-2-alkylthiouracil derivatives 4a-f.
Treatment of 4d with 1 mol tosyl chloride gives the corresponding mono
tosylate 5. On the other hand, with 2 mol it gives the ditosylate 6. T
reatment of 5 and/or 6 with sodium azide/dimethylformamide give 7 and
8 which could be reduced to the corresponding amino derivatives 9 and
10 by using triphenylphosphine/pyridine.