(2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid

Base Information

• Chemical Name: (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid
• CAS No.: 153829-66-4
• Molecular Formula: C₁₀H₁₃NO₄
• Molecular Weight: 211.218
• Mol file: 153829-66-4.mol

Synonyms:(2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid

Chemical Property of (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid

There total 16 articles about (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 63.0%

C12H15NO5 → (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid (153829-66-4) + (2R,3R)-erythro-N-acetyl-β-(4-methoxyphenyl)serine

Guidance literature:

With L-aminoacylase from Aspergillus oryzae; cobalt(II) chloride; sodium hydroxide; In water; at 37 ℃; for 36h; pH=7; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/ejoc.201402470

Reference yield: 35.0%

(+/-)-erythro-N-acetyl-β-(4-methoxyphenyl)serine → (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid (153829-66-4) + (2R,3R)-erythro-N-acetyl-β-(4-methoxyphenyl)serine

Guidance literature:

With cobalt(II) chloride; In water; at 33 - 41 ℃; for 6h; aminoacylase, pH = 7.0;

DOI:10.1248/cpb.41.1521

Reference yield:

tert-butyl (S,S)-2-amino-3-hydroxy-3-(4'-methoxyphenyl)-propanoate → C10H13NO4 + (2S,3S)-2-amino-3-hydroxy-3-(4-methoxyphenyl)propanoic acid (153829-66-4)

Guidance literature:

With hydrogenchloride; In water; at 20 ℃; for 3h; Overall yield = 62 %; Overall yield = 21 mg;

DOI:10.1016/j.tet.2014.06.057

upstream raw materials:

[(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

1-[N-(9-fluorenylmethyloxycarbonyl)-(1S)-1-amino-2-(4-methoxyphenyl)-2-oxoethyl]-4-methyl-2,6,7-trioxabicyclo[2.2.2]octane

ethyl α-hydroxyimino-β-oxo-4-methoxybenzenepropionate

ethyl 4-methoxybenzoylacetate

Downstream raw materials:

methyl (2S,3S)-(+)-2-bromo-3-hydroxy-3-(4-methoxyphenyl)propionate

(2S,3R)-methyl p-methoxycinnamate epoxide

methyl (2R,3S)-3-(4-methoxyphenyl)glycidate