dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate

Base Information

• Chemical Name: dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate
• CAS No.: 950580-20-8
• Molecular Formula: C₅₁H₅₄N₂O₄
• Molecular Weight: 759.001
• Mol file: 950580-20-8.mol

Synonyms:dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate

Chemical Property of dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate

There total 4 articles about dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate 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: 52.0%

methyl 2-{(S)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}acrylate (950580-16-2) + C25H27NO2 → dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate (950580-20-8) + dimethyl (2S,4R)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate (950580-21-9)

Guidance literature:

C₂₅H₂₇NO₂; With lithium diisopropyl amide; In hexane; Petroleum ether; at -30 ℃; for 0.5h;

methyl 2-{(S)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}acrylate; In hexane; Petroleum ether; at -30 - 20 ℃; Further stages.;

DOI:10.1016/j.tetasy.2007.06.010

Reference yield:

dimethyl (2S,4R)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate (950580-21-9) → dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate (950580-20-8)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; for 72h; Heating;

DOI:10.1016/j.tetasy.2007.06.010

Reference yield:

C25H27NO2 → dimethyl (2S,4S)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate (950580-20-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: LDA / tetrahydrofuran; petroleum ether / 1 h / -78 °C

1.2: ZnBr₂ / tetrahydrofuran; petroleum ether / 0.5 h / -78 °C

1.3: 56 percent / tetrahydrofuran; petroleum ether / 1 h / -78 °C

2.1: 85 percent / MsCl; (1,3-diazabicyclo[5.4.0]undecane / dioxane / 16 h / 60 °C

3.1: LDA / tetrahydrofuran; petroleum ether / -30 °C

3.2: 10 percent / tetrahydrofuran; petroleum ether / -30 - 20 °C

With methanesulfonyl chloride; lithium diisopropyl amide; In tetrahydrofuran; 1,4-dioxane; Petroleum ether; 3.2: Michael addition reaction;

DOI:10.1016/j.tetasy.2007.06.010

upstream raw materials:

dimethyl (2S,4R)-2,4-bis{(R)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}glutarate

methyl 2-{(S)-[N-benzyl-N-((S)-1-phenylethyl)amino]phenylmethyl}acrylate

Downstream raw materials:

dimethyl (2S,4S)-2,4-bis[(R)-phenyl-((S)-1-phenylethylamino)methyl]glutarate

(1R,2R,5R,6R)-2,6-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane

(1S,4R,5S,8R)-4,8-diphenyl-3,7-bis((S)-1-phenylethyl)-3,7-diazabicyclo[3.3.1]nonane-2,6-dione

(2S,4S)-2,4-bis[(R)-phenyl-((S)-1-phenylethylamino)methyl]pentane-1,5-diol