title: On the mechanism of lithiation of uridine derivatives with lithium dialkylamides.
abstract: Efficiency and regioselectivity (C-6 or C-5) in the lithiation of uridine derivatives were examined by using LDA (lithium diisopropylamide) and LTMP (lithium 2,2,6,6-tetramethylpiperidide). It revealed that rotation of the C-2' substituent caused steric hindrance on approaching the lithiating agent to the C-6 position, providing evidence that the lithiation takes place through their syn-conformers.
mesh_terms: D000577:Amides; D055598:Chemical Phenomena; D002621:Chemistry; D008094:Lithium; D010880:Piperidines; D013329:Structure-Activity Relationship; D014529:Uridine / Q000031:analogs & derivatives*
chemical_list: D000577:Amides; D010880:Piperidines; D008094:Lithium; D014529:Uridine