25488-27-1

Basic information

• Product Name: threo-L-(2S,3R)-β-methylphenylalanine
• Synonyms: threo-L-(2S,3R)-β-methylphenylalanine
• CAS NO: 25488-27-1
• Molecular Weight: 179.219
• Mol File: 25488-27-1.mol
• Article Data: 11

Chemical Properties

• Melting Point: 193-194 °C
• Boiling Point: 306.0±30.0 °C(Predicted)
• Density: 1.158±0.06 g/cm3(Predicted)
• CAS DataBase Reference: threo-L-(2S,3R)-β-methylphenylalanine(CAS DataBase Reference)
• NIST Chemistry Reference: threo-L-(2S,3R)-β-methylphenylalanine(25488-27-1)
• EPA Substance Registry System: threo-L-(2S,3R)-β-methylphenylalanine(25488-27-1)

Safety Data

• Hazardous Substances Data: 25488-27-1(Hazardous Substances Data)

Upstream product

• 25488-26-0 erythro-D-(2R,3R)-β-methylphenylalanine 
• 69015-75-4 (Z)-2-phenyl-4-(α-phenylethylidene)-5-(4H)-oxazolone 
• 128677-92-9 (2R)-azido-(3R)-phenylbutanoic acid 
• 128677-94-1 (2S,3R)-2-azido-3-phenylbutanoic acid 
• 4658-69-9 α-keto-β-phenylbutyric acid 
• 22122-01-6 2-Aethoxy-3-methyl-zimtsaeure-aethylester 
• 1449299-81-3 C₂₇H₂₁N₃O₃ 
• 591-50-4 iodobenzene 
• 585-71-7 (1-bromoethyl)benzne 
• 56-40-6 glycine 
• 128677-91-8 (4S)-3-(2'R,3'R)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone 
• 128677-89-4 (R)-4-Benzyl-3-((S)-3-phenyl-butyryl)-oxazolidin-2-one 
• 772-14-5 (R)-3-phenylbutyric acid 
• 143251-56-3 (R)-4-Benzyl-3-((2S,3R)-2-bromo-3-phenyl-butyryl)-oxazolidin-2-one 

Downstream Products

• 25488-26-0 erythro-D-(2R,3R)-β-methylphenylalanine 
• 145432-51-5 (βR)-N-(tert-butoxycarbonyl)-β-methyl-L-phenylalanine 

Relevant articles and documents

Stereoselective Synthesis of β-Branched Aromatic α-Amino Acids by Biocatalytic Dynamic Kinetic Resolution**

β-Branched noncanonical amino acids are valuable molecules in modern drug development efforts. However, they are still challenging to prepare due to the need to set multiple stereocenters in a stereoselective fashion, and contemporary methods for the synthesis of such compounds often rely on the use of rare-transition-metal catalysts with designer ligands. Herein, we report a highly diastereo- and enantioselective biocatalytic transamination method to prepare a broad range of aromatic β-branched α-amino acids. Mechanistic studies show that the transformation proceeds through dynamic kinetic resolution that is unique to the optimal enzyme. To highlight its utility and practicality, the biocatalytic reaction was applied to the synthesis of several sp3-rich cyclic fragments and the first total synthesis of jomthonic acid A.

(2R,1'S,2'R)- And (2S,1'S,2'R)-3-[2-mono(di,tri)fluoromethylcyclopropyl] alanines and their incorporation into hormaomycin analogues

Efficient and scalable syntheses of enantiomerically pure (2 R ,1' S ,2' R )- and (2 S ,1' S ,2' R )-3-[2-mono(di,tri)fluoromethylcyclopropyl] alanines 9a - c , as well as allo-D-threonine ( 4 ) and ( 2 S,3R)-β-methylphenylalanine (3), using the Belokon' approach with (S )- and (R )-2-[( N-benzylprolyl)amino]benzophenone [(S)- and (R)-10 ] as reusable chiral auxiliaries have been developed. Three new fluoromethyl analogues of the naturally occurring octadepsipeptide hormaomycin ( 1 ) with (fluoromethylcyclopropyl) alanine moieties have been synthesized and subjected to preliminary tests of their antibiotic activity.

An efficient and stereodivergent synthesis of threo- and erythro-β-methylphenylalanine. Resolution of each racemic pair by semipreparative HPLC

threo and erythro diastereoisomers of the constrained amino acid (βMe)Phe can be obtained separately on a multigram scale through a three-step synthesis from the corresponding Z and E isomers of 2-phenyl-4(α-phenylethylidene)-5(4H)-oxazolone. The 5(4H)-ox