2-Methoxy-D-Phenylalanine

Base Information

• Chemical Name: 2-Methoxy-D-Phenylalanine
• CAS No.: 170642-31-6
• Molecular Formula: C10H13NO3
• Molecular Weight: 195.218
• DSSTox Substance ID: DTXSID70442716
• Mol file: 170642-31-6.mol

Synonyms:2-Methoxy-D-Phenylalanine;170642-31-6;(R)-2-Amino-3-(2-methoxyphenyl)propanoic acid;(2R)-2-AMINO-3-(2-METHOXYPHENYL)PROPANOIC ACID;SCHEMBL4595466;DTXSID70442716;MFCD03788081;AKOS016843679;AM83384;AS-58553;N12455;A882007

Chemical Property of 2-Methoxy-D-Phenylalanine

Chemical Property:

• Boiling Point: 337.2 °C at 760 mmHg
• Flash Point: 157.8 °C
• PSA: 72.55000
• Density: 1.209 g/cm³
• LogP: 1.34990
• XLogP3: -0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 195.08954328
• Heavy Atom Count: 14
• Complexity: 196

Purity/Quality:

98%min ^*data from raw suppliers

2-Methoxy-D-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=CC=CC=C1CC(C(=O)O)N
• Isomeric SMILES: COC1=CC=CC=C1C[C@H](C(=O)O)N

Technology Process of 2-Methoxy-D-Phenylalanine

There total 12 articles about 2-Methoxy-D-Phenylalanine 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: 77.0%

(Z)-2-hydroxy-3-(2-methoxy-phenyl)-acrylic acid (207910-76-7) → (2R)-2-amino-3-(2-methoxyphenyl)propanoic acid (170642-31-6)

Guidance literature:

With D-glucose; nicotinamide adenine dinucleotide phosphate; ammonium chloride; In methanol; at 20 ℃; for 24h; pH=9; enantioselective reaction; Microbiological reaction;

DOI:10.1002/adsc.201600682

Reference yield: 71.0%

2-Amino-N-((1S,2S)-2-hydroxy-1-methyl-2-phenyl-ethyl)-3-(2-methoxy-phenyl)-N-methyl-propionamide → (2R)-2-amino-3-(2-methoxyphenyl)propanoic acid (170642-31-6)

Guidance literature:

In 1,4-dioxane; water; for 22h; Heating;

DOI:10.1021/ja9624073

Reference yield:

o-Methoxybenzyl bromide (52289-93-7) + 2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide (170115-96-5) → pseudoephedrine (90-82-4,7009-81-6,90-83-5,6912-63-6) + (2R)-2-amino-3-(2-methoxyphenyl)propanoic acid (170642-31-6)

Guidance literature:

With water; lithium chloride; lithium diisopropyl amide; Yield given. Multistep reaction;

DOI:10.1021/ja00137a034

upstream raw materials:

o-Methoxybenzyl bromide

2-amino-N-[(1S,2S)-2-hydroxy-1-methyl-2-phenylethyl]-N-methylacetamide

D-N-acetyl-2-methoxyphenylalanine

(2-methoxyphenyl)methanol

Downstream raw materials:

(R)-2-amino-3-(2-methoxyphenyl)propan-1-ol

N-tert-butoxycarbonyl-D-2-methoxyphenylalanyl-L-2-methoxyphenylalanine methyl ester

N-tert-butoxycarbonyl-L-2-methoxyphenylalanyl-D-2-methoxyphenylalanine methyl ester

N-tert-butoxycarbonyl-D-2-methoxyphenylalanyl-D-2-methoxyphenylalanine methyl ester

Refernces

• 1、 Walton, Curtis J. W.,Parmeggiani, Fabio,Barber, Janet E. B.,McCann, Jenna L.,Turner, Nicholas J.,Chica, Roberto A.. "Engineered Aminotransferase for the Production of d-Phenylalanine Derivatives Using Biocatalytic Cascades". . p. 470 - 474. Retrieved 2017/12/15.
• 2、 Myers, Andrew G.,Gleason, James L.,Yoon, Taeyoung,Kung, Daniel W.. "Highly practical methodology for the synthesis of D- and L-α-amino acids, N-protected α-amino acids, and N-methyl-α-amino acids". . p. 656 - 673. Retrieved 2007/10/03.