Abstract Both enantiomers of 2′-deoxy-4′-thiouridine (9) and 15, 4′-thiothymidine (10) and 16, and 2′-deoxy-4′-thiocytidine (14) and 17 and 1-(2-deoxy-4-thio-β-D-erythro- pentafuranosyl)-5-trifluoromethyluracil (11) were synthesized. The key coupling reactions were performed by the reaction of D-or L-enantiomers of ethyl 5-O-acetyl-3-O-(tert- butyldimethylsilyl)-2-deoxy-4-thio-α, β3-xylofuranoside (1)) or 18 and 2, 4-bis ( ...