Synthesis of 4'-selenoribonucleosides.
We report herein the synthesis and structural aspects of 4'selenouridine (11) and 4'-selenocytidine (13), novel nucleoside derivatives. 4'Selenouridine (11) was synthesized via the stereoselective seleno-Pummerer reaction between an appropriately protected selenoxide 9 and a persilylated uracil. 4'-Selenocytidine (13) was prepared from 4'selenouridine derivative 10. To the best of our knowledge, this is the first example concerning introduction of a heterocycle into the alpha- position of a seleno atom.
Inagaki
Yusuke
Y
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita12, Nishi 6, Kitaku, Sapporo 0600812, Japan.
Minakawa
Noriaki
N
Matsuda
Akira
A
D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D016566:Organoselenium Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D012263:Ribonucleosides / Q000138:chemical synthesis* / Q000737:chemistry; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry
C528351:4'-selenocytidine; C528350:4'-selenouridine; D016566:Organoselenium Compounds; D012263:Ribonucleosides; D003562:Cytidine; D014529:Uridine