153829-66-4

Basic information

• Product Name: (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid
• Synonyms: (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid
• CAS NO: 153829-66-4
• Molecular Weight: 211.218
• Mol File: 153829-66-4.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid(153829-66-4)
• EPA Substance Registry System: (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid(153829-66-4)

Safety Data

• Hazardous Substances Data: 153829-66-4(Hazardous Substances Data)

Upstream product

• 104-92-7 1-bromo-4-methoxy-benzene 
• 714951-38-9 tert-butyl (R,R,R)-2-hydroxy-3-[N-benzyl-N-(α-methylbenzyl)amino]-3-(4'-methoxyphenyl)propanoate 
• 53484-52-9 tert-butyl (E)-3-(4-methoxyphenyl)prop-2-enoate 
• 2881-83-6 ethyl 4-methoxybenzoylacetate 
• 27331-97-1 ethyl α-hydroxyimino-β-oxo-4-methoxybenzenepropionate 
• 206191-13-1 1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane 
• 206191-20-0 [(1S,2S)-2-Hydroxy-2-(4-methoxy-phenyl)-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-ethyl]-carbamic acid 9H-fluoren-9-ylmethyl ester 

Downstream Products

• 153829-67-5 methyl (2S,3S)-(+)-2-bromo-3-hydroxy-3-(4-methoxyphenyl)propionate 
• 137173-40-1 (2S,3R)-methyl p-methoxycinnamate epoxide 
• 105560-93-8 methyl (2R,3S)-3-(4-methoxyphenyl)glycidate 

Relevant articles and documents

Total Synthesis of Skyllamycins A–C

The skyllamycins are a family of highly functionalized non-ribosomal cyclic depsipeptide natural products which contain the extremely rare α-OH-glycine functionality. Herein the first total synthesis of skyllamycins A–C is reported, together with the biofilm inhibitory activity of the natural products. Linear peptide precursors for each natural product were prepared through an efficient solid-phase route incorporating a number of synthetic modified amino acids. A novel macrocyclization step between a C-terminal amide and an N-terminal glyoxylamide moiety served as a key transformation to install the unique α-OH-glycine unit and generate the natural products in the final step of the synthesis.

Biocatalytic Synthesis of Enantiopure β-Methoxy-β-arylalanine Derivatives

Chiral β-hydroxy-β-arylalanine and β-methoxy-β-arylalanine derivatives, which occur widely in marine nature products, were stereoselectively synthesized with 99 % ee values. The two erythro isomers were prepared by L- or D-aminoacylase-catalyzed resolution of the corresponding N-acetyl derivatives, whereas the two threo isomers were obtained only by D-aminoacylase-catalyzed resolution of the derivatives. erythro-β-Hydroxy-β-arylalanine derivatives were prepared by diastereoselective hydrogenation of ethyl 2-(hydroxyimino)-3-oxo-3-arylpropanoates, which were in turn acquired by the oximation of ethyl 3-oxo-3-arylpropanoates with ethyl nitrite in the presence of nano-K2CO3 with yields of 72 % to 80 %. β-Methoxy-β-arylalanine derivatives were synthesized through Williamson reactions between the corresponding β-hydroxy-β-arylalanines and iodomethane with silver oxide as base.

A new enantioselective synthesis of (2R,3S)-3-(4-methoxyphenyl)glycidic ester via the enzymatic hydrolysis of erythro-N-acetyl-β-(4- methoxyphenyl)serine

Enantioselective synthesis of (2R,3S)-3-(4-methoxyphenyl)glycidic ester ((2R,3S)-1) via the enzymatic hydrolysis of erythro-N-acetyl-β-(4- methoxyphenyl)serine (9) was investigated. Treatment of the obtained α- amino acid (-)-10 with NaNO2-KBr-dilute H2SO4, esterification, and subsequent oxiran-ring closure of the halohydrin gave the target compound (2R,3S)-1 with high enantiomeric excess (94% ee).