582302-77-0Relevant articles and documents
Scalable Synthesis of the Potent HIV Inhibitor BMS-986001 by Non-enzymatic Dynamic Kinetic Asymmetric Transformation (DYKAT)
Ortiz, Adrian,Benkovics, Tamas,Beutner, Gregory L.,Shi, Zhongping,Bultman, Michael,Nye, Jeffrey,Sfouggatakis, Chris,Kronenthal, David R.
, p. 7185 - 7188 (2015/06/08)
Abstract Described herein is the synthesis of BMS-986001 by employing two novel organocatalytic transformations: 1)a highly selective pyranose to furanose ring tautomerization to access an advanced intermediate, and 2)an unprecedented small-molecule-mediated dynamic kinetic resolution to access a variety of enantiopure pyranones, one of which served as a versatile building block for the multigram, stereoselective, and chromatography-free synthesis of BMS-986001. The synthesis required five chemical transformations and resulted in a 44 % overall yield. Good dynamic: Described is the synthesis of BMS-986001 by employing two novel organocatalytic transformations: a highly selective pyranose to furanose ring tautomerization, and an unprecedented small-molecule-mediated dynamic kinetic asymmetric transformation (DYKAT) to access enantiopure pyranones. BMS-986001 was synthesized in five steps in an overall yield of 44 %. Bz=benzoyl.
De novo asymmetric bio- and chemocatalytic synthesis of saccharides - Stereoselective formal O-glycoside bond formation using palladium catalysis
Comely, Alex C.,Eelkema, Rienk,Minnaard, Adriaan J.,Feringa, Ben L.
, p. 8714 - 8715 (2007/10/03)
A novel integrated bio- and chemocatalytic approach to the de novo catalytic asymmetric synthesis of saccharides has been developed. Acetoxypyranones obtained enantiopure by enzymatic resolution have been shown to undergo highly stereoselective palladium-catalyzed formal O-glycoside bond formation. The combination of these protocols can be applied to the iterative asymmetric catalytic synthesis of saccharides. Copyright
