3-Acetyl-N-benzyloxycarbonyl-4-O-benzyl-L-tyrosine Methyl Ester

Base Information

• Chemical Name: 3-Acetyl-N-benzyloxycarbonyl-4-O-benzyl-L-tyrosine Methyl Ester
• CAS No.: 105205-69-4
• Molecular Formula: C27H27NO6
• Molecular Weight: 461.514
• DSSTox Substance ID: DTXSID40552497
• Wikidata: Q82432793
• Mol file: 105205-69-4.mol

Synonyms:105205-69-4;3-Acetyl-N-benzyloxycarbonyl-4-O-benzyl-L-tyrosine Methyl Ester;methyl (2S)-3-(3-acetyl-4-phenylmethoxyphenyl)-2-(phenylmethoxycarbonylamino)propanoate;DTXSID40552497;J-001359;Methyl 3-acetyl-O-benzyl-N-[(benzyloxy)carbonyl]-L-tyrosinate;(S)-Methyl 3-(3-acetyl-4-(benzyloxy)phenyl)-2-(((benzyloxy)carbonyl)amino)propanoate

Chemical Property of 3-Acetyl-N-benzyloxycarbonyl-4-O-benzyl-L-tyrosine Methyl Ester

Chemical Property:

• PSA: 94.42000
• LogP: 4.68310
• Solubility.: Dichloromethane
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 12
• Exact Mass: 461.18383758
• Heavy Atom Count: 34
• Complexity: 656

Purity/Quality:

98%Min ^*data from raw suppliers

3-Acetyl-N-benzyloxycarbonyl-4-O-benzyl-L-tyrosine Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=C(C=CC(=C1)CC(C(=O)OC)NC(=O)OCC2=CC=CC=C2)OCC3=CC=CC=C3
• Isomeric SMILES: CC(=O)C1=C(C=CC(=C1)C[C@@H](C(=O)OC)NC(=O)OCC2=CC=CC=C2)OCC3=CC=CC=C3
• Uses: Protected L-DOPA (D533751) derivative.

Technology Process of 3-Acetyl-N-benzyloxycarbonyl-4-O-benzyl-L-tyrosine Methyl Ester

There total 10 articles about 3-Acetyl-N-benzyloxycarbonyl-4-O-benzyl-L-tyrosine Methyl Ester 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: 93.0%

benzyl bromide (100-39-0) + L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3) → L-3-(3-acetyl-4-(benzyloxy)phenyl)-N-(benzyloxycarbonyl)alanine methyl ester (105205-69-4) + (R)-3-(3-Acetyl-4-benzyloxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester (105205-69-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 23 ℃; for 6h; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00232a044

Reference yield: 93.0%

benzyl bromide (100-39-0) + L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3) → L-3-(3-acetyl-4-(benzyloxy)phenyl)-N-(benzyloxycarbonyl)alanine methyl ester (105205-69-4) + (R)-3-(3-Acetyl-4-benzyloxy-phenyl)-2-benzyloxycarbonylamino-propionic acid methyl ester (105205-69-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 23 ℃; for 6h; Yields of byproduct given. Title compound not separated from byproducts;

DOI:10.1021/jo00232a044

Reference yield: 60.0%

benzyl bromide (100-39-0) + L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester (110774-03-3) → L-3-(3-acetyl-4-(benzyloxy)phenyl)-N-(benzyloxycarbonyl)alanine methyl ester (105205-69-4)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; potassium carbonate; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1021/jm050910x

upstream raw materials:

benzyl bromide

L-3-(3-acetyl-4-hydroxyphenyl)-N-(benzyloxycarbonyl)alanine methyl ester

L-tyrosine

(S)-3-(3-acetyl-4-hydroxyphenyl)-2-aminopropanoic acid hydrochloride

Downstream raw materials:

(S)-2-Benzyloxycarbonylamino-3-[4-benzyloxy-3-(1-hydroxy-ethyl)-phenyl]-propionic acid methyl ester

L-3-(3-acetyl-4-(benzyloxy)phenyl)-N-(benzyloxycarbonyl)-N-methylalanine methyl ester

L-3-(3-methoxy-4-(benzyloxy)phenyl)-N-(benzyloxycarbonyl)alanine methyl ester

3-O-methyldopa