Tetrahedron p. 1675 - 1684 (1985)
Update date:2022-09-26
Topics:
Hayakawa, Hiroyuki
Tanaka, Hiromichi
Miyasaka, Tadashi
2',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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