Synthesis of 2',3'-dideoxy-3'-fluorothymidine using individual anomers of 1,5-di-O-benzoyl-2,3-dideoxy-3-fluoro-D-erythro-pentofuranose as glycosylating agents

Article abstract of DOI:10.1055/s-1993-25925

A convenient preparation of α- and β-anomers of 1,5-di-O-benzoyl-2,3-dideoxy-3-fluoro-D-erythro-pentofuranose is described. Each anomer is studied as the glycosylating agent in the reaction with bis-trimethylsilylated thymine in the presence of trimethylsilyl triflate. Under optimum conditions, 2',3'-dideoxy-3'-fluorothymidine (FLT) and its α-anomer are isolated in 64 and 25% yields, respectively.