(2S,3R)-2-benzyl-3,4-iminobutanoic acid methyl ester

Base Information

• Chemical Name: (2S,3R)-2-benzyl-3,4-iminobutanoic acid methyl ester
• CAS No.: 349148-47-6
• Molecular Formula: C₁₂H₁₅NO₂
• Molecular Weight: 205.257
• Mol file: 349148-47-6.mol

Synonyms:(2S,3R)-2-benzyl-3,4-iminobutanoic acid methyl ester

Chemical Property of (2S,3R)-2-benzyl-3,4-iminobutanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R)-2-benzyl-3,4-iminobutanoic acid methyl ester

There total 8 articles about (2S,3R)-2-benzyl-3,4-iminobutanoic acid 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: 97.0%

(2S,3R)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester (349148-43-2) → (2S,3R)-2-benzyl-3,4-iminobutanoic acid methyl ester (349148-47-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 2h;

DOI:10.1021/jo0014055

Reference yield:

benzyl bromide (100-39-0) → (2S,3R)-2-benzyl-3,4-iminobutanoic acid methyl ester (349148-47-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 61 percent / tetrahydrofuran; hexane / 6 h

2.1: acetyl chloride / methanol / 3 h / 0 °C

2.2: CuCO₃*Cu(OH)2 / H₂O / 3 h / 70 °C

3.1: Na₂CO₃ / H₂O / 4 h / 20 °C

4.1: DCC / 1,2-dimethoxy-ethane

5.1: NaBH₄ / tetrahydrofuran / 18 h / 0 - 20 °C

6.1: 79 percent / DEAD; PPh₃ / tetrahydrofuran / 3 h / 0 °C

7.1: 97 percent / H₂ / Pd/C / methanol / 2 h

With sodium tetrahydroborate; hydrogen; sodium carbonate; acetyl chloride; dicyclohexyl-carbodiimide; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; water; 6.1: Intramolecular Mitsunobu reaction;

DOI:10.1021/jo0014055

Reference yield:

(2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester (130622-08-1) → (2S,3R)-2-benzyl-3,4-iminobutanoic acid methyl ester (349148-47-6)

Guidance literature:

Multi-step reaction with 7 steps

1.1: LiHMDS / tetrahydrofuran; hexane / 2 h / -78 °C

1.2: 61 percent / tetrahydrofuran; hexane / 6 h

2.1: acetyl chloride / methanol / 3 h / 0 °C

2.2: CuCO₃*Cu(OH)2 / H₂O / 3 h / 70 °C

3.1: Na₂CO₃ / H₂O / 4 h / 20 °C

4.1: DCC / 1,2-dimethoxy-ethane

5.1: NaBH₄ / tetrahydrofuran / 18 h / 0 - 20 °C

6.1: 79 percent / DEAD; PPh₃ / tetrahydrofuran / 3 h / 0 °C

7.1: 97 percent / H₂ / Pd/C / methanol / 2 h

With sodium tetrahydroborate; hydrogen; sodium carbonate; acetyl chloride; dicyclohexyl-carbodiimide; triphenylphosphine; lithium hexamethyldisilazane; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; water; 6.1: Intramolecular Mitsunobu reaction;

DOI:10.1021/jo0014055

upstream raw materials:

(2S,3R)-2-benzyl-3,4-(benzyloxycarbonylimino)-butanoic acid methyl ester

benzyl bromide

(2R)-2-tert-butoxycarbonylamino-succinic acid dimethyl ester

(2R,3S)-N-tert-butyloxycarbonyl-3-benzylaspartic acid dimethyl ester