Synthesis and radical reaction of 1'-phenylselenonucleosides.
The 1'alpha-phenylselenouridine derivative (4) was successfully synthesized via enolization at the 1'-position of the 3',5'-O-TIPDS-2'-ketouridine (1). After the introduction of a vinylsilyl tether as an intramolecular radical acceptor at the 2'-hydroxy group of 4, its atom-transfer radical cyclization reaction, followed by the treatment with TBAF gave 1'alpha-vinyluridine derivative (10). Using this procedure, 1'alpha-vinyluridine (11) and -cytidine (14) were successfully synthesized.
Kodama
T
T
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Nomura
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M
Shuto
S
S
Matsuda
A
A
D003562:Cytidine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D005609:Free Radicals / Q000737:chemistry; D008722:Methods; D015394:Molecular Structure; D017646:Organosilicon Compounds / Q000138:chemical synthesis / Q000737:chemistry; D011741:Pyrimidine Nucleosides / Q000138:chemical synthesis* / Q000737:chemistry*; D014529:Uridine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry
C430814:1'-vinylcytidine; C430813:1'-vinyluridine; D005609:Free Radicals; D017646:Organosilicon Compounds; D011741:Pyrimidine Nucleosides; D014753:Vinyl Compounds; D003562:Cytidine; D014529:Uridine