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

Base Information

• Chemical Name: 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoic acid
• CAS No.: 287935-81-3
• Molecular Formula: C₂₀H₂₄NO₆P
• Molecular Weight: 405.387
• Mol file: 287935-81-3.mol

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

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

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}propanoic acid

There total 4 articles about 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoic acid 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: 90.5%

methyl 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoate (287935-86-8) → 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoic acid (287935-81-3)

Guidance literature:

With sodium hydroxide; In methanol; at 20 ℃; for 16h;

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}propanoic acid (287935-81-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; In methanol; 1: Addition / 2: Hydrolysis;

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}propanoic acid (287935-81-3)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With sodium hydroxide; N,O-bis-(trimethylsilyl)-acetamide; In methanol; 1: Addition / 2: Hydrolysis;

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

upstream raw materials:

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

methyl 2-benzylacrylate

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

[1-[[(phenylmethoxy)carbonyl]amino]ethyl]phosphinic acid

Downstream raw materials:

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

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

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