title: Studies on antitumor agents. IX. Synthesis of 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine.
abstract: A practical synthesis of 3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine (1), a candidate antitumor agent for clinical testing, was developed from 2'-deoxy-5-iodouridine (3). Benzylation of 2'-deoxy-5-iodo-5'-O-trityluridine (14) with benzyl bromide and sodium hydride in tetrahydrofuran gave the 3'-O-derivative (16). Benzoylation of 16 afforded the N3-benzoyl derivative (17). Coupling of 17 with trifluoromethylcopper, prepared from bromotrifluoromethane and copper powder in the presence of 4-dimethylaminopyridine, gave the 5-trifluoromethyl derivative (19) minimally contaminated with the 5-pentafluoroethyl compound. Deprotection of 19 furnished 1.
authors.forename: J
authors.initials: J
authors.lastname: Yamashita
authors.forename: H
authors.initials: H
authors.lastname: Matsumoto
authors.forename: K
authors.initials: K
authors.lastname: Kobayashi
authors.forename: K
authors.initials: K
authors.lastname: Noguchi
authors.forename: M
authors.initials: M
authors.lastname: Yasumoto
authors.forename: T
authors.initials: T
authors.lastname: Ueda
mesh_terms: D000970:Antineoplastic Agents / Q000138:chemical synthesis*; D055598:Chemical Phenomena; D002621:Chemistry; D013936:Thymidine / Q000031:analogs & derivatives*; D014271:Trifluridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology
chemical_list: D000970:Antineoplastic Agents; C062357:3'-O-benzyl-2'-deoxy-5-trifluoromethyluridine; D014271:Trifluridine; D013936:Thymidine