157722-44-6

Basic information

• Product Name: Benzenepropanoic acid, β-aMino-α-hydroxy-, Methyl ester, (αR,βR)-
• Synonyms: Benzenepropanoic acid, β-aMino-α-hydroxy-, Methyl ester, (αR,βR)-;Methyl (2R,3R)-3-amino-2-hydroxy-3-phenylpropanoate;Methyl (2R,3R)-phenylisoserine;benzenepropanoic acid, -amino-a-hydroxy-, methyl ester, (ar,r)-
• CAS NO: 157722-44-6
• Molecular Formula: C₁₀H₁₃NO₃
• Molecular Weight: 195.22
• Mol File: 157722-44-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 343.0±42.0 °C(Predicted)
• Appearance: /
• Density: 1.212±0.06 g/cm3(Predicted)
• PKA: 10.35±0.45(Predicted)
• CAS DataBase Reference: Benzenepropanoic acid, β-aMino-α-hydroxy-, Methyl ester, (αR,βR)-(CAS DataBase Reference)
• NIST Chemistry Reference: Benzenepropanoic acid, β-aMino-α-hydroxy-, Methyl ester, (αR,βR)-(157722-44-6)
• EPA Substance Registry System: Benzenepropanoic acid, β-aMino-α-hydroxy-, Methyl ester, (αR,βR)-(157722-44-6)

Safety Data

• Hazardous Substances Data: 157722-44-6(Hazardous Substances Data)

Upstream product

• 1595172-39-6 (2R,3R)-3-azido-3-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propanal 
• 104-55-2 3-phenyl-propenal 
• 1595172-56-7 (2R,3R)-methyl 3-azido-3-phenyl-2-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)propanoate 
• 19190-80-8 methyl trans-3-phenylglycidate 
• 103-26-4 Methyl cinnamate 
• 39878-87-0 d(-)-alpha-phenylglycine chloride hydrochloride 
• 875-74-1 (R)-phenylglycine 
• 157722-45-7 methyl 3-amino-2-keto-3-phenylpropionate 
• 127053-44-5 Methyl (2R,3R)-(-)-2-hydroxy-3-azido-3-phenyl-propionate 

Relevant articles and documents

Metal-organocatalytic tandem azide addition/oxyamination of aldehydes for the enantioselective synthesis of β-amino α-hydroxy esters

The tandem reaction of α,β-unsaturated aldehydes with trimethylsilyl azide and 2,2,6,6-tetramethylpiperidin-1-yloxy in the presence of chiral amines and iron complexes as the catalysts in a one-pot reaction enantioselectively afforded β-azido α-oxyaminated aldehydes. Further synthetic modification of the product afforded β-amino α-hydroxy esters in good yields with good diastereo- and enantioselectivities.

CHEMO-ENZYMATIC SYNTHESIS OF ALL ISOMERIC 3-PHENYLSERINES AND -ISOSERINES

The synthesis of all isomers of 3-phenylserines and 3-phenylisoserines in enantiomerically pure form is presented.Diastereomerically pure educts (threo/erythro-2-azido-3-butanoyloxy-3-phenyl-propionic esters, threo/erythro-3-azido-2-butanoyloxy-3-phenylpropionic esters, threo-2-butanoylamino-3-butanoyloxy-3-phenylpropionic ester, erythro-3-butanoylamino-2-butanoyloxy-3-phenyl-propionamide) were prepared from cinnamic acid derivatives or via aldol condensations of benzaldehyde and suitable enolates in few steps.These racemates were resolved with lipases from Candida cylindracea (CC) and Pseudomonas fluorescens (P) and the obtained products were hydrogenated to 3-phenylserines and -isoserines.The influence of the acyl group in the enzymatic resolution of erythro-3-azido-2-acyloxy-3-phenylpropionic esters was investigated.