2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester

Base Information

• Chemical Name: 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester
• CAS No.: 287935-82-4
• Molecular Formula: C₃₆H₃₉N₂O₈P
• Molecular Weight: 658.688
• Mol file: 287935-82-4.mol

Synonyms:2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester

Chemical Property of 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester

There total 4 articles about 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl 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: 63.1%

L-tyrosine benzyl ester p-toluenesulfonate (53587-11-4,97984-63-9) + 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoic acid (287935-81-3) → 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester (287935-82-4)

Guidance literature:

With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; dichloromethane; at 20 ℃; for 0.75h;

DOI:10.1002/(SICI)1099-1344(200002)43:2<103::AID-JLCR294>3.0.CO;2-I

Reference yield:

methyl 2-benzylacrylate (3070-71-1) → 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester (287935-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92.2 percent / N,O-bistrimethylsilylacetamide / 70 °C

2: 90.5 percent / aq. NaOH / methanol / 16 h / 20 °C

3: 63.1 percent / diisopropylethylamine; HOBt; EDC / CH₂Cl₂; tetrahydrofuran / 0.75 h / 20 °C

With sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 1: Addition / 2: Hydrolysis / 3: Acylation;

DOI:10.1002/(SICI)1099-1344(200002)43:2<103::AID-JLCR294>3.0.CO;2-I

Reference yield:

(R)-1-(N-benzyloxycarbonylamino)ethylphosphinic acid (115115-40-7) → 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine benzyl ester (287935-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 92.2 percent / N,O-bistrimethylsilylacetamide / 70 °C

2: 90.5 percent / aq. NaOH / methanol / 16 h / 20 °C

3: 63.1 percent / diisopropylethylamine; HOBt; EDC / CH₂Cl₂; tetrahydrofuran / 0.75 h / 20 °C

With sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; dichloromethane; 1: Addition / 2: Hydrolysis / 3: Acylation;

DOI:10.1002/(SICI)1099-1344(200002)43:2<103::AID-JLCR294>3.0.CO;2-I

upstream raw materials:

L-tyrosine benzyl ester p-toluenesulfonate

2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoic acid

methyl 2-benzylacrylate

(R)-1-(N-benzyloxycarbonylamino)ethylphosphinic acid

Downstream raw materials:

2(S)-benzyl-3-[hydroxy(1'(R)-aminoethyl)phosphinyl]propanoyl-L-tyrosine

2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine