Nucleophilic substitution of 4'-acetoxy-4'-thionucleosides: a new access to 4'-substituted 4'-thiothymidines.
A new method for the synthesis of 4'-substituted 4'-thiothymidines has been developed. This synthetic method consists of 1) diacetoxylation of 4',5'-unsaturated 4'-thiothymidine derivative 9 with Pb(OAc)(4), and 2) Lewis acid-promoted nucleophilic substitution of the resulting 4'-acetoxy nucleoside 10 with silicon reagents. This novel method enabled us to introduce carbon-substituents or heteroatom-substituents to the 4'-position.
Haraguchi
Kazuhiro
K
School of Pharmaceutical Sciences, Showa University, 1-5-8 Hatanodai, Shinagawa-ku, Tokyo 142-8555, Japan.
Shimada
Hisashi
H
Tanaka
Hiromichi
H
D001671:Biochemistry / Q000379:methods; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D013936:Thymidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
D013872:Thionucleosides; C070456:4'-thiothymidine; D013936:Thymidine