Kodama T, Nomura M, Shuto S, Matsuda A
Graduate School of Pharmaceutical Sciences, Hokkaido University, Kita-12, Nishi-6, Kita-ku, Sapporo 060-0812, Japan.
Nucleic Acids Symp Ser. 2000(44):109-10. doi: 10.1093/nass/44.1.109.
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.
通过对3'，5'-O-三异丙基二硅基-2'-酮基尿苷（1）的1'-位进行烯醇化反应，成功合成了1'α-苯硒基尿苷衍生物（4）。在4的2'-羟基处引入乙烯基硅烷基链作为分子内自由基受体后，其原子转移自由基环化反应，随后用四丁基氟化铵处理，得到1'α-乙烯基尿苷衍生物（10）。采用该方法，成功合成了1'α-乙烯基尿苷（11）和1'α-乙烯基胞苷（14）。
