85451-46-3Relevant academic research and scientific papers
SYNTHETIC ROUTE TO 5-SUBSTITUTED URIDINES VIA A NEW TYPE OF DESULFURIZATIVE STANNYLATION
Tanaka, Hiromichi,Hayakawa, Hiroyuki,Obi, Kikoh,Miyasaka, Tadashi
, p. 4187 - 4196 (2007/10/02)
Phenylthio 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-tetramethylpiperidine.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.
DESULFURIZATIVE STANNYLATION OF URACIL DERIVATIVES
Tanaka, Hiromichi,Hayakawa, Hiroyuki,Obi, Kikoh,Miyasaka, Tadashi
, p. 6229 - 6232 (2007/10/02)
Phenylthio group in the C-6 or C- position of uracil moiety can be removed by radical mediated stannylation with tributyltin hydride followed by protonolysis, providing a new route to 5-substituted uridines.
"UMPOLUNG" OF REACTIVITY AT THE C-6 POSITION OF URIDINE: A SIMPLE AND GENERAL METHOD FOR 6-SUBSTITUTED URIDINES
Tanaka, Hiromichi,Hayakawa, Hiroyuki,Miyasaka, Tadashi
, p. 2635 - 2642 (2007/10/02)
Lithiated 2',3'-O-isopropylidene-5'-O-methoxymethyl-uridine was found to react with a variety of electrophilic reagents regiospecifically at the C-6 position.The protecting groups of the ribose moiety in the 6-functionalized products were concurrently rem
