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

Base Information

Chemical Name:2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine
CAS No.:287935-87-9
Molecular Formula:C₂₉H₃₃N₂O₈P
Molecular Weight:568.563
Hs Code.:

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

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

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

There total 5 articles about 2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine 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: 90.2%

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

: 287935-87-9
2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine

Guidance literature:: With sodium hydroxide; In methanol; at 20 ℃; for 8h;
DOI:10.1002/(SICI)1099-1344(200002)43:2<103::AID-JLCR294>3.0.CO;2-I

Reference yield:

: 3070-71-1
methyl 2-benzylacrylate

: 287935-87-9
2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine

Guidance literature:: Multi-step reaction with 4 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

4: 90.2 percent / aq. NaOH / methanol / 8 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 / 4: Hydrolysis;
DOI:10.1002/(SICI)1099-1344(200002)43:2<103::AID-JLCR294>3.0.CO;2-I

Reference yield:

: 115115-40-7
(R)-1-(N-benzyloxycarbonylamino)ethylphosphinic acid

: 287935-87-9
2(R,S)-benzyl-3-{hydroxy[1'(R)-(N-benzyloxycarbonylamino)ethyl]phosphinyl}propanoyl-L-tyrosine

Guidance literature:: Multi-step reaction with 4 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

4: 90.2 percent / aq. NaOH / methanol / 8 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 / 4: Hydrolysis;
DOI:10.1002/(SICI)1099-1344(200002)43:2<103::AID-JLCR294>3.0.CO;2-I