Reaction of the 4'-benzenesulfonyl derivatives of thymidine with organosilicon and organoaluminum reagents.
With an aim to develop a new approach to synthesize 4'-substituted nucleosides, reactions of thymidine derivatives having a benzenesulfonyl leaving group at the 4'-position with organosilicon and organoaluminum reagents were investigated. Two substrates 4alpha (alpha-L-isomer) and 4 beta (beta-D-isomer) were prepared for this purpose. Although reaction of 4alpha with organosilicon reagents gave preferentially the 4'-substituted (allyl and N(3)) beta-D-nucleoside, its reaction with AlMe(3) gave the 4'-methyl-alpha-L-thymidine as the major product. On the other hand, the substrate 4beta, upon reacting with AlMe(3), furnished the desired 4'-methylthymidine exclusively in high yield.
Shimada
Hisashi
H
School of Pharmaceutical Sciences, Showa University, Tokyo 142-8555, Japan.
Kikuchi
Satoshi
S
Okuda
Saori
S
Haraguchi
Kazuhiro
K
Tanaka
Hiromichi
H
D000535:Aluminum / Q000737:chemistry*; D007202:Indicators and Reagents; D017646:Organosilicon Compounds / Q000737:chemistry*; D013936:Thymidine / Q000737:chemistry*
D007202:Indicators and Reagents; D017646:Organosilicon Compounds; D000535:Aluminum; D013936:Thymidine