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

Base Information

• Chemical Name: 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-3-iodotyrosine methyl ester
• CAS No.: 287935-83-5
• Molecular Formula: C₃₀H₃₄IN₂O₈P
• Molecular Weight: 708.487
• Mol file: 287935-83-5.mol

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

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

There total 4 articles about 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-3-iodotyrosine 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: 70.6%

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-3-iodotyrosine methyl ester (287935-83-5)

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-3-iodotyrosine methyl ester (287935-83-5)

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: 70.6 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-3-iodotyrosine methyl ester (287935-83-5)

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: 70.6 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:

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

methyl 2-benzylacrylate

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

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

Downstream raw materials:

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