Di-O-tert-butyldiphenylsilyl (BDPS)-thymidine (2) was converted to α-bromo-3', 5'-di-O-BDPS-thymidine (3) by photobromination. Crude 3 was hydrolyzed to the α-hydroxythymidine derivative 4 which was oxidized with MnO₂ to the 5-formyluracil nucleoside 5. Fluorination of 4 with diethylamino-sulfur trifluoride afforded the protected α-fluorothymidine 6. Similarly, 5 was converted into the α, α-difluorothymine nucleoside 7. These protected fluorothymidines (6 and 7) were deblocked by treatment with tetra-n-butylammonium fluoride to give α-fluorothymidine(8, F-TDR) and α, α-difluorothymidine (9, F₂-TDR).