title: Synthesis of 4'-substituted cordycepins.
abstract: Synthesis of 4'-substituted analogues of cordycepin was carried out. Electrophilic addition of N-iodosuccinimide/benzoic acid to 2',5'-bis-O-(tert-butyldimethyl-silyl)-3',4'-unsaturated adenosine (5) enabled the introduction of a leaving group to the 4'-position. The resulting product 7 was converted to 4'-(benzoyloxy) cordycepin (8) upon removal of the 3'-iodine atom. Compound 8 serves as a common precursor for the synthesis of the title compounds through nucleophilic substitution using organoaluminum and organosilicon reagents.
authors.affiliation: School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Kubota
authors.forename: Mayumi
authors.initials: M
authors.lastname: Kunikata
authors.forename: Rumi
authors.initials: R
authors.lastname: Ohsawa
authors.forename: Yuria
authors.initials: Y
authors.lastname: Odajima
authors.forename: Kazuhiro
authors.initials: K
authors.lastname: Haraguchi
authors.forename: Hiromichi
authors.initials: H
authors.lastname: Tanaka
mesh_terms: D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: C520192:4'-(benzoyloxy)cordycepin; D003839:Deoxyadenosines; C058120:cordycepin