Hiroyuki Hayakawa, Hiromichi Tanaka, Tadashi Miyasaka
1985
Citations
0
Influential Citations
15
Citations
Journal
Tetrahedron
Abstract
Abstract 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.