Synthetic route to 5-substituted uridines via a new type of desulfurizative stannylation
1986; Elsevier BV; Volume: 42; Issue: 15 Linguagem: Inglês
10.1016/s0040-4020(01)87642-0
ISSN1464-5416
AutoresHiromichi Tanaka, Hiroyuki Hayakawa, Kikoh Obi, Miyasaka Tadashi,
Tópico(s)Synthesis of heterocyclic compounds
Resumophenylthio group at the C-6 position of uridine serves as the protecting group during lithiation at the C-5 position with lithium 2,2,6,6-tetramethylpiperidide. Reactions of the resulting C-5 lithiated species with various types of electrophiles furnish 5-substituted 6-phenylthiouridine derivatives. The phenylthio group in these products can be removed by a new type of desulfurizative stannylation with tributyltin hydride followed by protonolysis. The whole sequence constitutes a new route to 5-substituted uridines. Application of this method to 2'-deoxyuridine is also described.
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