3491-28-9Relevant articles and documents
Compact reaction-module on a pad for scalable flow-production of organophosphates as drug scaffolds
Kang, In Seok,Kim, Dong-Pyo,Ramanjaneyulu, Bandaru T.,Vidyacharan, Shinde,Yang, Yu Dong,Yim, Se Jun
, p. 973 - 978 (2020/03/13)
Continuous pharmaceutical manufacturing receives intense attention as an alternative way to meet flexible market needs with the assurance of higher safety and quality control. Here, we report a compact reaction-module on a pad (CRP, 170 × 170 × 1.2 mm) for scale-up production of drug precursors in a continuous-flow. The CRP system was devised by stacking 9 films of the patterned polyimide to integrate micro-flow circuits, combining the functions of the even distribution of feeds, being completely mixed in less than a few milliseconds. A methodology of using a highly reactive species for the single-step synthesis of α-phosphonyloxy ketone, a drug scaffold, required the synthesis time of a few seconds in microfluidics. The fast reaction in the single CRP was capable of producing 19.2 g h-1 drug precursor, which indicates a solid step toward kilogram-scale pharmaceutical manufacturing in small footage.
I2O5/DBU mediated direct α-phosphoryloxylation of ketones with H-phosphonates leading to α-hydroxyketone phosphates
Liu, Chunli,Wei, Wei,Yang, Daoshan,Zheng, Yuanyuan,Bi, Yanshuai,Chen, Min,Wang, Hua
, p. 6901 - 6906 (2015/08/24)
A simple and convenient procedure has been developed for the construction of α-hydroxyketone phosphates via I2O5/DBU mediated direct α-phosphoryloxylation of ketones with H-phosphonates. This new reaction proceeds through three steps involving α-iodination of ketones, oxidation of H-phosphonates, and nucleophilic substitution of α-iodo ketones to access a series of α-hydroxyketone phosphates of biological importance.
Cyanide-catalyzed additions of acyl phosphonates to aldehydes: A new acyl donor for benzoin-type reactions
Bausch, Cory C.,Johnson, Jeffrey S.
, p. 1207 - 1211 (2007/10/03)
Acyl phosphonates have been utilized as new acyl donors for cyanide-catalyzed benzoin-type reactions. Cyanation of acyl phosphonates, followed by a [1,2]-phosphoryl migration generates the active acyl anion intermediate. The presumed (cyano)phosphate anion reacts with a variety of aryl aldehydes to yield phosphate ester-protected, unsymmetrical benzoins in good to excellent yields. The unsymmetrical benzoin product can be obtained after deprotection of the phosphate ester with an aqueous amine solution.
