132785-26-3

Basic information

• Product Name: (2S,3R)-3-hydroxy-N-phthaloylphenylalanine methyl ester
• Synonyms: (2S,3R)-3-hydroxy-N-phthaloylphenylalanine methyl ester
• CAS NO: 132785-26-3
• Molecular Weight: 325.321
• Mol File: 132785-26-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: (2S,3R)-3-hydroxy-N-phthaloylphenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3R)-3-hydroxy-N-phthaloylphenylalanine methyl ester(132785-26-3)
• EPA Substance Registry System: (2S,3R)-3-hydroxy-N-phthaloylphenylalanine methyl ester(132785-26-3)

Safety Data

• Hazardous Substances Data: 132785-26-3(Hazardous Substances Data)

Upstream product

• 14380-85-9 (S)-methyl 2-(1,3-dioxoisoindolin-2-yl)-3-phenylpropanoate 
• 1001-62-3 bis(methanesulfonyl)peroxide 
• 132785-20-7 (2R,3R)-3-bromo-N-phthaloylphenylalanine methyl ester 
• 196092-86-1 (R)-3-Bromo-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-3-phenyl-propionic acid methyl ester 

Downstream Products

• 6254-48-4 (2S,3R)-3-phenylserine 

Relevant articles and documents

Synthesis of Benzylic Alcohols by C-H Oxidation

Selective methylene C-H oxidation for the synthesis of alcohols with a broad scope and functional group tolerance is challenging due to the high proclivity for further oxidation of alcohols to ketones. Here, we report the selective synthesis of benzylic alcohols employing bis(methanesulfonyl) peroxide as an oxidant. We attempt to provide a rationale for the selectivity for monooxygenation, which is distinct from previous work; a proton-coupled electron transfer mechanism (PCET) may account for the difference in reactivity. We envision that our method will be useful for applications in the discovery of drugs and agrochemicals.

SYNTHESIS OF HOMOCHIRAL HYDROXY-α-AMINO ACID DERIVATIVES

Treatment of N-phthaloyl-α-amino acid methyl esters with N-bromosuccinimide, followed by reaction with silver nitrate in aqueous acetone, affords homochiral hydroxy-α-amino acid derivatives, the stereochemistry of which is predetermined by that of the starting amino acids.