Lithiation of 5,6-dihydrouridine: a new route to 5-substituted uridines
1985; Elsevier BV; Volume: 41; Issue: 9 Linguagem: Inglês
10.1016/s0040-4020(01)96481-6
ISSN1464-5416
AutoresHiroyuki Hayakawa, Hiromichi Tanaka, Tadashi Miyasaka,
Tópico(s)Organic and Inorganic Chemical Reactions
Resumo2',3'-O-Isopropylidene-5'-O-methoxymethyl-5,6-dihydrouridine (2) was found to serve as an “amide α-anion” upon lithiation with LDA. Reactions of the anion with acid chlorides followed by phenylselenation and oxidative elimination furnished 5-acyluridines. For the preparation of 5-alkyluridines, initial introduction of phenylselenenyl group at the C-5 of 2 appeared to be effective. Alkylation of its α-selenenyl carbanion and subsequent generation of 5,6-double bond produced 5-alkyluridines. These routes constitute a new entry to 5-substituted uridines.
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