The synthesis of pharmacologically active 2'-deoxynucleoside analog, namely, 2',3'-dideoxythymidine (I) and 3'-fluoro-3'-deoxythymidine (II) is described. The proposed approach consist in the condensation of corresponding thioglycosides with silylated thymine using N-bromosuccinimide as a promoter. In the case of compound II, it was shown that the yield and stereoselectivity of this process depend on the equivalent ratio of silylated base and solvent.