Tyrosine, 3-hydroxy-O-methyl-

Base Information

• Chemical Name: Tyrosine, 3-hydroxy-O-methyl-
• CAS No.: 35296-56-1
• Molecular Formula: C₁₀H₁₃NO₄
• Molecular Weight: 211.218
• UNII: U75PY6L5YN
• DSSTox Substance ID: DTXSID10963096
• Nikkaji Number: J2.042.551B
• Mol file: 35296-56-1.mol

Synonyms:3-hydroxy-4-methoxyphenylalanine;4-methoxytyrosine;p-methoxy-L-tyrosine;para-methoxy-L-tyrosine

Chemical Property of Tyrosine, 3-hydroxy-O-methyl-

Chemical Property:

• Boiling Point: 409.7±45.0 °C(Predicted)
• PKA: 2.23±0.20(Predicted)
• PSA: 92.78000
• Density: 1.321±0.06 g/cm3(Predicted)
• LogP: 1.05550
• XLogP3: -2.4
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 211.08445790
• Heavy Atom Count: 15
• Complexity: 222

Purity/Quality:

99% ^*data from raw suppliers

3-Hydroxy-O-methyl-L-tyrosine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC1=C(C=C(C=C1)CC(C(=O)O)N)O
• Isomeric SMILES: COC1=C(C=C(C=C1)C[C@@H](C(=O)O)N)O
• Uses: 3-Hydroxy-O-methyl-L-tyrosine is used in the preparation of tyrosine-based components of natural products such as saframycin MX1 and its analogs, which are naturally potent anti-tumor agents currently under clinical development.

Technology Process of Tyrosine, 3-hydroxy-O-methyl-

There total 5 articles about Tyrosine, 3-hydroxy-O-methyl- 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:

2-tert-butoxycarbonylamino-3-(3-hydroxy-4-methoxy-phenyl)-propionic acid → 3-(3-hydroxy-4-methoxyphenyl)-L-alanine (35296-56-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 0.5h;

DOI:10.1016/j.tetlet.2004.03.112

Reference yield:

2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester (574735-09-4) → 3-(3-hydroxy-4-methoxyphenyl)-L-alanine (35296-56-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 100 percent / lithium hydroxide; water / dimethylformamide / 20 °C

2: diphenyldiselenide; hydrogen peroxide / CH₂Cl₂; H₂O / 20 °C

3: 5 mg / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

With lithium hydroxide; diphenyl diselenide; water; dihydrogen peroxide; trifluoroacetic acid; In dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/j.tetlet.2004.03.112

Reference yield:

N-(tert-butyloxycarbonyl)-3-(3-formyl-4-methoxyphenyl)-L-alanine (133641-14-2) → 3-(3-hydroxy-4-methoxyphenyl)-L-alanine (35296-56-1)

Guidance literature:

Multi-step reaction with 2 steps

1: diphenyldiselenide; hydrogen peroxide / CH₂Cl₂; H₂O / 20 °C

2: 5 mg / trifluoroacetic acid / CH₂Cl₂ / 0.5 h / 20 °C

With diphenyl diselenide; dihydrogen peroxide; trifluoroacetic acid; In dichloromethane; water;

DOI:10.1016/j.tetlet.2004.03.112

upstream raw materials:

levodopa

2-tert-butoxycarbonylamino-3-(3-formyl-4-methoxy-phenyl)-propionic acid methyl ester

N-(tert-butyloxycarbonyl)-3-(3-formyl-4-methoxyphenyl)-L-alanine

S-Adenosyl-L-methionine

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