A FACILE, ALTERNATIVE SYNTHESIS OF 4'-THIOARABINONUCLEOSIDES AND THEIR BIOLOGICAL-ACTIVITIES

4'-Thioarabinonucleosides, which are potential antiviral agents, were synthesized from D-glucose. 1,4-Anhydro-4-thioarabitol (8), which can be derived from diacetone glucose in nine steps, was subjected to Pumm erer rearrangement after protection of the hydroxyl groups to give 1-O -acetyl-4-thioarabinose (II), which was condensed with nucleobases to give 4'-thioarabinonucleosides. The 5-substituted-4'-thioaraU (6a-e) d erivatives showed anti-HSV-1 activity (ED50 = 0.43-3.50 mu g/mL). 4'-T hioaraG (6h) and 2,6-diaminopurine 4'-thioarabinonucleoside (4'-thioar aDAP, 6g) showed antiviral activity against several herpes viruses and were particularly potent against human cytomegalovirus (0.010 and 0.0 22 mu g/mL, respectively).