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Synthesis and radical reaction of 1'-phenylselenonucleosides
1Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Nucleic Acids Symposium Series
|August 9, 2003
Abstract:
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.