53791-83-6Relevant academic research and scientific papers
Asymmetric Synthesis of the Cyclohexyl Fragment in RORγt Inhibitor (BMS-986251) Enabled by a Dynamic Kinetic Resolution of Hageman's Ester
Coombs, John R.,Gallagher, William P.,González-Bobes, Francisco,Guerrero, Carlos A.,Joe, Candice L.,Katipally, Kishta,Mudryk, Boguslaw M.,Rupasinghe, Sanjeewa,Zhu, Jason
, (2021/11/30)
The cyclohexyl fragment 1 in BMS-986251 was synthesized starting from Hagemann's ester 2 in 7 steps and 5 isolations. The route is highlighted by a dynamic kinetic resolution (DKR), a telescoped enol nonaflation followed by a palladium-catalyzed carbonylation, and a rhodium-catalyzed directed diastereoselective olefin hydrogenation. The optimized process was demonstrated on 1 kg scale, with an overall 51% yield and >99% ee and dr.
Development of a Scalable Synthetic Route to BMS-986251. Part 1: Synthesis of the Cyclohexane Dicarboxylate Fragment
Coombs, John R.,Eastgate, Martin D.,Gallagher, William P.,Gangu, Aravind S.,Gonzalez-Bobes, Francisco,Joe, Candice L.,Kalidindi, Srinivas,Kopp, Nathaniel,Kuppusamy, Sankar,Mudryk, Boguslaw,Nagappan, Vedhachalam,Palani, Senthil,Ponnusamy, Muthukrishnan,Rupasinghe, Sanjeewa,Tendulkar, Shankar,Vaidyanathan, Rajappa,Venu, Alla,Vinodini, Arun
, p. 1547 - 1555 (2021/07/19)
The cyclohexane dicarboxylate unit of BMS-986251 (1), a potent and efficacious RORγt inverse agonist, was synthesized starting from Hagemann's ester in seven chemical transformations with five isolated intermediates. The synthesis involved an enzymatic ki
Enantioselective synthesis of the hexahydronaphthalene nucleus of (-)-compactin from ethyl (1R,2S)-2-methyl-4-oxocyclohexanecarboxylate and 2-(3-nitropropyl)-1,3-dioxolane as four carbon bifunctional annelating agent
Barco,Benetti,Bianchi,Casolari,Pollini,Romagnoli,Spalluto,Zanirato
, p. 11743 - 11754 (2007/10/02)
An enantioselective approach to the synthesis of the hexahydronaphthalene nucleus of natural compactin is described. The key elements of the synthesis are as follows: (i) the preparation of the chiral starting material through enzymatic resolution of the
