(2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine

Base Information

• Chemical Name: (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine
• CAS No.: 858367-23-4
• Molecular Formula: C₂₅H₃₂N₂O₅
• Molecular Weight: 440.539
• Mol file: 858367-23-4.mol

Synonyms:(2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine

Chemical Property of (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine

There total 11 articles about (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine 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:

{[(E,3S,4S)-4-methyl-1-nitrohex-1-en-3-yloxy]methyl}benzene (858366-96-8) + (R,E)-methyl 2-(benzylideneamino)propanoate (647833-63-4) → (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine (858367-23-4)

Guidance literature:

With silver(I) acetate; triethylamine; In acetonitrile; at 20 ℃; for 5h;

DOI:10.1002/anie.200462497

Reference yield:

(2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol (858366-85-5) → (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine (858367-23-4)

Guidance literature:

Multi-step reaction with 4 steps

1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 5 h / -70 - -60 °C

2: triethylamine / 16 h / 20 °C

3: methanesulfonyl chloride; ethyldiisopropylamine / CH₂Cl₂ / -70 - 20 °C

4: triethylamine; AgOAc / acetonitrile / 5 h / 20 °C

With oxalyl dichloride; silver(I) acetate; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetonitrile; 2: Henry reaction;

DOI:10.1002/anie.200462497

Reference yield:

L-isoleucine (73-32-5,959215-79-3,18875-42-8) → (2S,3R,4S,5S)-3-[(S)-1-(benzyloxy)-2-methybutyl]-2-methoxycarbonyl-2-methyl-4-nitro-5-phenylpyrrolidine (858367-23-4)

Guidance literature:

Multi-step reaction with 8 steps

1: NaNO₂; H₂SO₄ / H₂O / 24 h / 0 °C

2: p-toluenesulfonic acid monohydrate / methanol / 24 h / 45 °C

3: NaH / tetrahydrofuran; dimethylformamide / 0 - 20 °C

4: lithium aluminum hydride / diethyl ether / 3 h / 20 °C

5: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 5 h / -70 - -60 °C

6: triethylamine / 16 h / 20 °C

7: methanesulfonyl chloride; ethyldiisopropylamine / CH₂Cl₂ / -70 - 20 °C

8: triethylamine; AgOAc / acetonitrile / 5 h / 20 °C

With lithium aluminium tetrahydride; oxalyl dichloride; sulfuric acid; silver(I) acetate; sodium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium nitrite; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile; 3: Williamson reaction / 6: Henry reaction;

DOI:10.1002/anie.200462497

upstream raw materials:

{[(E,3S,4S)-4-methyl-1-nitrohex-1-en-3-yloxy]methyl}benzene

(R,E)-methyl 2-(benzylideneamino)propanoate

(2S,3S)-2-Benzyloxy-3-methyl-pentan-1-ol

methyl (2S,3S)-2-(benzyloxy)-3-methylpentanoate

Downstream raw materials:

(2S,3R,4S,5S)-3-[(1S,2S)-1-(benzyloxy)-2-methylbutyl]-2-methyl-4-nitro-5-phenylpyrrolidine-2-carboxylic acid

methyl 5-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}pentanoate

methyl 6-{(2S,3R,4S,5S)-3-[(2S)-1-benzyloxy-2-methylbutyl]-2-methyl-4-nitro-5-phenyl-prolylamino}hexanoate

[(2S,3R,4S,5S)-3-(1-(S)-benzyloxy-2-methylbutyl)-1-N-[(1,3-dioxo-2,3-dihydro-1H-inden-2-yl)acetyl]-2-methyl-4-nitro-5-phenyl-prolyl]-β-alanine