186839-95-2Relevant academic research and scientific papers
Nucleosides and Nucleotides. 163. Synthesis of 3′-β-Branched Uridine Derivatives via Intramolecular Reformatsky-Type Reaction Promoted by Samarium Diiodide
Ichikawa, Satoshi,Shuto, Satoshi,Minakawa, Noriaki,Matsuda, Akira
, p. 1368 - 1375 (2007/10/03)
A novel efficient method for the synthesis of 3′-β-branched uridines starting from uridine was developed, in which a SmI2-promoted intramolecular Reformatsky-type reaction was effectively used. 5′-O-(Bromoacetyl)-3′-ketouridine derivatives 12, 26, and 27 were synthesized from uridine and were subjected to an intramolecular Reformatsky-type reaction. When 12, 26, and 27 were treated with 2.0 equiv of SmI2 in THF at -78°C, intramolecular carbon-carbon bond formation at the 3′-β-position proceeded smoothly to give the corresponding 3′,5′-lactones 14, 28, and 29 in high yields, respectively. Treatment of 28 with NH3/MeOH gave the 3′-β-branched uridine derivative 32 quantitatively, which was then deprotected to give 3′-C-(carbamoylmethyl)uridine (33).
