(2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester

Base Information

• Chemical Name: (2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester
• CAS No.: 180193-77-5
• Molecular Formula: C₃₆H₃₉NO₃
• Molecular Weight: 533.711
• Mol file: 180193-77-5.mol

Synonyms:(2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester

Chemical Property of (2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester

There total 5 articles about (2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl 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: 60.0%

phenylmagnesium bromide (100-58-3) + (E)-(S)-5-Dibenzylamino-4-oxo-6-phenyl-hex-2-enoic acid butyl ester (750638-95-0) → (2S,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester + (2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester (180193-77-5)

Guidance literature:

With 2,3-dimercapto-succinic acid; copper(I) bromide; In tetrahydrofuran; at -20 ℃; Yields of byproduct given;

DOI:10.1016/0040-4039(96)00828-3

Reference yield:

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) → (2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester (180193-77-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 64 percent / K₂CO₃, NaOH / H₂O

2: 81 percent / BuLi / tetrahydrofuran / -78 °C

3: 87 percent / DBU / tetrahydrofuran / -15 °C / Wadsworth-Emmons condensation

4: 60 percent / Et₂Al, CuBr, DMS / tetrahydrofuran / -20 °C

With sodium hydroxide; n-butyllithium; 2,3-dimercapto-succinic acid; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(I) bromide; In tetrahydrofuran; water;

DOI:10.1016/0040-4039(96)00828-3

Reference yield:

N,N-dibenzyl-L-phenylalanine benzyl ester (111138-83-1) → (2R,5S)-5-Dibenzylamino-4-oxo-2,6-diphenyl-hexanoic acid butyl ester (180193-77-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 81 percent / BuLi / tetrahydrofuran / -78 °C

2: 87 percent / DBU / tetrahydrofuran / -15 °C / Wadsworth-Emmons condensation

3: 60 percent / Et₂Al, CuBr, DMS / tetrahydrofuran / -20 °C

With n-butyllithium; 2,3-dimercapto-succinic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; copper(I) bromide; In tetrahydrofuran;

DOI:10.1016/0040-4039(96)00828-3

upstream raw materials:

phenylmagnesium bromide

(E)-(S)-5-Dibenzylamino-4-oxo-6-phenyl-hex-2-enoic acid butyl ester

L-phenylalanine

N,N-dibenzyl-L-phenylalanine benzyl ester

Downstream raw materials:

(2R,4S,5S)-5-Dibenzylamino-4-hydroxy-2,6-diphenyl-hexanoic acid butyl ester

Refernces