84765-97-9Relevant academic research and scientific papers
Synthesis of C6-Substituted Purine Nucleoside Analogues via Late-Stage Photoredox/Nickel Dual Catalytic Cross-Coupling
Perkins, James J.,Shurtleff, Valerie W.,Johnson, Alayna M.,El Marrouni, Abdellatif
, p. 662 - 666 (2021)
Nucleoside analogues have been and continue to be extremely important compounds in drug discovery. Despite the significant effort dedicated to their synthesis, medicinal chemistry campaigns around these structures are often hampered by synthetic challenges. We describe a strategy for the functionalization of purine nucleosides via photoredox and nickel-catalyzed sp2-sp3 cross-coupling. The conditions described herein allow for coupling of unprotected nucleosides with readily available alkyl bromides, providing opportunities for their application to parallel medicinal chemistry.
Organocatalyzed, Visible-Light Photoredox-Mediated, One-Pot Minisci Reaction Using Carboxylic Acids via N-(Acyloxy)phthalimides
Sherwood, Trevor C.,Li, Ning,Yazdani, Aliza N.,Dhar, T. G. Murali
, p. 3000 - 3012 (2018/03/09)
An improved, one-pot Minisci reaction has been developed using visible light, an organic photocatalyst, and carboxylic acids as radical precursors via the intermediacy of in situ-generated N-(acyloxy)phthalimides. The conditions employed are mild, demonstrate a high degree of functional group tolerance, and do not require a large excess of the carboxylic acid reactant. As a result, this reaction can be applied to drug-like scaffolds and molecules with sensitive functional groups, enabling late-stage functionalization, which is of high interest to medicinal chemistry.
SYNTHESIS OF 6-ALKYL AND 6-ARYL SUBSTITUTED 9-β-D-RIBOFURANOSYL PURINES VIA THE NICKEL CATALYZED COUPLING OF GRIGNARD REAGENTS TO 2',3',5'-Tris-O-(t-BUTYLDIMETHYLSILYL)-9-β-D-RIBOFURANOSYL-6-CHLOROPURINE
Bergstrom, Donald E.,Reday, P. Anantha
, p. 4191 - 4194 (2007/10/02)
A series of 6-substituted purine nucleosides have been synthesized in moderate yield by the nickel catalyzed cross coupling reaction between alkyl- and aryl-Grignard reagents and 2',3',5'-tris-O-(t-butyldimethylsilyl)-9-β-D-ribofuranosyl-6-chloropurine.
