Synthesis of 4'-substituted cordycepins.
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.
Kubota
Yutaka
Y
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
Kunikata
Mayumi
M
Ohsawa
Rumi
R
Odajima
Yuria
Y
Haraguchi
Kazuhiro
K
Tanaka
Hiromichi
H
D003839:Deoxyadenosines / Q000138:chemical synthesis* / Q000737:chemistry
C520192:4'-(benzoyloxy)cordycepin; D003839:Deoxyadenosines; C058120:cordycepin