(2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester

Base Information

• Chemical Name: (2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester
• CAS No.: 861432-39-5
• Molecular Formula: C₂₉H₃₄N₂O₄
• Molecular Weight: 474.6
• Mol file: 861432-39-5.mol

Synonyms:(2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester

Chemical Property of (2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester

There total 6 articles about (2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic 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: 92.0%

(2S,3S)-2-amino-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester (861432-41-9) + di-tert-butyl dicarbonate (24424-99-5) → (2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester (861432-39-5)

Guidance literature:

With triethylamine; In 1,4-dioxane; at 20 ℃; for 1h;

DOI:10.1016/j.tet.2005.04.046

Reference yield:

methyl (R)-3-(dibenzylamino)-3-phenylpropanoate (861432-34-0) → (2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester (861432-39-5)

Guidance literature:

Multi-step reaction with 4 steps

1.1: bis(trimethylsilyl)amide / tetrahydrofuran; toluene / 1 h / -78 °C

1.2: tetrahydrofuran; toluene / -78 °C

2.1: trifluoroacetic acid / CH₂Cl₂ / 2 h

3.1: hydrogen; W-2 Raney nickel / methanol / 4 h / 20 °C

4.1: 92 percent / triethylamine / dioxane / 1 h / 20 °C

With W-2 Raney nickel; hydrogen; hexamethyldisilazide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene;

DOI:10.1016/j.tet.2005.04.046

Reference yield:

(2S,3S)-3-Dibenzylamino-2-hydrazino-3-phenyl-propionic acid methyl ester → (2S,3S)-2-(tert-butoxycarbonylamino)-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester (861432-39-5)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogen; W-2 Raney nickel / methanol / 4 h / 20 °C

2: 92 percent / triethylamine / dioxane / 1 h / 20 °C

With W-2 Raney nickel; hydrogen; triethylamine; In 1,4-dioxane; methanol;

DOI:10.1016/j.tet.2005.04.046

upstream raw materials:

(2S,3S)-2-amino-3-(dibenzylamino)-3-phenylpropanoic acid methyl ester

di-tert-butyl dicarbonate

methyl (R)-3-(dibenzylamino)-3-phenylpropanoate

methyl (2S,3S)-3-(dibenzylamino)-2-[N',N''-(di-tert-butoxycarbonyl)-hydrazino]-3-phenylpropanoate

Downstream raw materials:

(2S,3S)-3-amino-2-(tert-butoxycarbonylamino)-3-phenylpropanoic acid methyl ester