220871-52-3Relevant articles and documents
Convenient method for synthesis of N-protected α-amino epoxides: Key intermediates for HIV protease inhibitors
Blacker, A. John,Roy, Mita,Hariharan, Sivaramkrishanan,Headley, Catherine,Upare, Abhay,Jagtap, Ashutosh,Wankhede, Karuna,Mishra, Sushil Kumar,Dube, Dagadu,Bhise, Sanjay,Vishwasrao, Sandesh,Kadam, Nitin
, p. 331 - 338 (2011)
A convenient method for synthesis of 2R,3S and 2S,3S N-Boc phenylalanine epoxides using readily available allylamine is described. Previous methods employed multistep synthetic routes from l-phenyl alanine that include use of m-chloroperbenzoic acid (m-CPBA) and a chromatographic method for purification of the desired diastereomers. Column purification could be eliminated by bringing in much improvement in the existing process. The process was further enhanced by replacing m-CPBA with oxone, an ecofriendly reagent advantageous for commercial application. The overall green process discussed involves the recovery and recycling of enantiomers of chiral allyl amines and judicial separation of diastereomers of the epoxides using simple economical methods.
Synthesis of chiral iodo-N,O-acetonide aminal scaffolds via an efficient cascade reaction of amino acid-derived epoxides
Paige Souder,Evans, Zachary M.,Driver, Joshua A.,Pozzo, Eric J.,Lampkins, Andrew J.
scheme or table, p. 6908 - 6910 (2012/02/15)
Novel amino acid-derived iodo-N,O-acetonide aminals were developed as chiral, non-epimerizable scaffolds to facilitate complex molecule synthesis. These scaffolds are readily prepared from commercially available amino acid derivatives in ≤6 steps, contain an orthogonally-protected β-hydroxy amine moiety, and feature a directly reactive alkyl-iodide group for facile substitution chemistry. Further, a novel ring opening/cyclization cascade reaction was developed to prepare these compounds efficiently (59-72%) from readily available epoxide derivatives.
Synthesis and antiviral activity of a series of HIV-1 protease inhibitors with functionality tethered to the P1 or P1'phenyl substituents: X-ray crystal structure assisted design
Thompson,Fitzgerald,Holloway,Emini,Darke,McKeever,Schleif,Quintero,Zugay,Tucker,Schwering,Homnick,Nunberg,Springer,Huff
, p. 1685 - 1701 (2007/10/02)
By tethering of a polar hydrophilic group to the P1 or P1' substituent of a Phe-based hydroxyethylene isostere, the antiviral potency of a series of HIV protease inhibitors was improved. The optimum enhancement of anti-HIV activity was observed with the 4-morpholinylethoxy substituent. The substituent effect is consistent with a model derived from inhibitor docked in the crystal structure of the native enzyme. An X-ray crystal structure of the inhibited enzyme determined to 2.25 A verifies the modeling predictions.
