4-Thiofuranoid glycals: versatile synthons for stereoselective synthesis of 4'-thionucleosides.
Beta-anomers of 4'-thionucleosides have been synthesized stereoselectively, through PhSeCl- or N-iodosuccimide (NIS)-initiated electrophilic glycosidation to 3,5-O-(di-t-butylsilylene)-4-thiofuranoid glycal (1). This synthetic method has been applied to the synthesis of those analogues branched at the anomeric position using 1-C-carbon-substituted 3,5-O-(tetraisopropyldisiloxane-1,3-diyl)-4-thiofuranoid glycals (11-14) prepared based on lithiation of 10.
Haraguchi
Kazuhiro
K
School of Pharmaceutical Sciences, Showa University, Shinagawa-ku, Tokyo, Japan. harakazu@pharm.showa-u.ac.jp
Takahashi
Haruhiko
H
Tanaka
Hiromichi
H
D005663:Furans; D007202:Indicators and Reagents; D008958:Models, Molecular; D013237:Stereoisomerism; D013438:Sulfhydryl Compounds; D013872:Thionucleosides / Q000138:chemical synthesis* / Q000737:chemistry*
D005663:Furans; D007202:Indicators and Reagents; D013438:Sulfhydryl Compounds; D013872:Thionucleosides