99388-49-5Relevant academic research and scientific papers
A SIMPLE AND GENERAL ENTRY TO 5-SUBSTITUTED URUDINES BASED ON THE REGIOSELECTIVE LITHIATHION CONTROLLED BY A PROTECTING GROUP IN THE SUGAR MOIETY
Hayakawa, Hiroyuki,Tanaka, Hiromichi,Obi, Kikoh,Itoh, Masayuki,Miyasaka, Tadashi
, p. 87 - 90 (2007/10/02)
Lithiathion of 2',3',5'-tris-O-(tert-butyldimethylsilyl)uridine with sec-BuLi/TMEDA occurs at the C-5 position with a high regioselectivity and subsequent reactions of the resulting C-5 lithiated species with a variety of electrophiles provides a general entry to 5-substituted uridines.
LITHIATION OF 5,6-DIHYDROURIDINE: A NEW ROUTE TO 5-SUBSTITUTED URIDINES
Hayakawa, Hiroyuki,Tanaka, Hiromichi,Miyasaka, Tadashi
, p. 1675 - 1684 (2007/10/02)
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.
