[3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid benzyl ester
• CAS No.: 188054-58-2
• Molecular Formula: C₃₂H₂₉N₂O₃P
• Molecular Weight: 520.568
• Mol file: 188054-58-2.mol

Synonyms:[3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid benzyl ester

Chemical Property of [3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid benzyl ester

There total 2 articles about [3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid benzyl 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: 88.0%

(S)-2-(((benzyloxy)carbonyl)amino)butanoic acid (42918-86-5,1145-79-5,2900-20-1,20395-87-3) + cyanomethylene triphenylphosphorane (16640-68-9) → [3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propyl]-carbamic acid benzyl ester (188054-58-2)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; for 4h; Ambient temperature;

DOI:10.1016/S0040-4039(96)02488-4

Reference yield:

(cyanomethyl)triphenylphosphonium chloride (4336-70-3) → [3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propyl]-carbamic acid benzyl ester (188054-58-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / Et₃N / CH₂Cl₂ / 0.67 h

2: 88 percent / EDCI, DMAP / CH₂Cl₂ / 4 h / Ambient temperature

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(96)02488-4

Reference yield: 69.0%

N-benzyloxycarbonyl-L-valyl-L-valine (19542-54-2) + [3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propyl]-carbamic acid benzyl ester (188054-58-2) → (1-{1-[1-[3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ5-phosphanylidene)-propylcarbamoyl]-2-methylpropylcarbamoyl]-2-methylpropylcarbamoyl}-2-methylpropyl)-carbamic acid benzyl ester (188054-60-6)

Guidance literature:

[3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propyl]-carbamic acid benzyl ester; With hydrogen; palladium on activated charcoal; In ethyl acetate; at 20 ℃; for 5h;

N-benzyloxycarbonyl-L-valyl-L-valine; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In dichloromethane; ethyl acetate; at 0 - 20 ℃; for 2.16667h;

DOI:10.1016/S0040-4020(03)00860-3

upstream raw materials:

(S)-2-(((benzyloxy)carbonyl)amino)butanoic acid

cyanomethylene triphenylphosphorane

(cyanomethyl)triphenylphosphonium chloride

Downstream raw materials:

(S)-4-Amino-3-oxo-2-(triphenyl-λ⁵-phosphanylidene)-hexanenitrile

(1-{1-[1-[3-cyano-1-ethyl-2-oxo-3-(triphenyl-λ⁵-phosphanylidene)-propylcarbamoyl]-2-methylpropylcarbamoyl]-2-methylpropylcarbamoyl}-2-methylpropyl)-carbamic acid benzyl ester

2-(2-{3-[2-(2-benzyloxycarbonylamino-3-methylbutyrylamino)-3-methyl-butyrylamino]-2-oxo-pentanoylamino}-4-methylpentanoylamino)-3-methylbutyric acid benzyl ester

2-(2-{3-[2-(2-amino-3-methylbutyrylamino)-3-methyl-butyrylamino]-2-oxo-pentanoylamino}-4-methylpentanoylamino)-3-methylbutyric acid