(R,S)-4-benzyloxycarbonylamino-5-(4-nitrophenyl)-2,2-difluoro-3-hydroxypentanoic acid ethyl ester

Base Information

• Chemical Name: (R,S)-4-benzyloxycarbonylamino-5-(4-nitrophenyl)-2,2-difluoro-3-hydroxypentanoic acid ethyl ester
• CAS No.: 119920-86-4
• Molecular Formula: C₂₁H₂₂F₂N₂O₇
• Molecular Weight: 452.412
• Mol file: 119920-86-4.mol

Synonyms:(R,S)-4-benzyloxycarbonylamino-5-(4-nitrophenyl)-2,2-difluoro-3-hydroxypentanoic acid ethyl ester

Chemical Property of (R,S)-4-benzyloxycarbonylamino-5-(4-nitrophenyl)-2,2-difluoro-3-hydroxypentanoic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,S)-4-benzyloxycarbonylamino-5-(4-nitrophenyl)-2,2-difluoro-3-hydroxypentanoic acid ethyl ester

There total 5 articles about (R,S)-4-benzyloxycarbonylamino-5-(4-nitrophenyl)-2,2-difluoro-3-hydroxypentanoic acid ethyl 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: 30.0%

Ethyl bromodifluoroacetate (667-27-6) + [(S)-1-Formyl-2-(4-nitro-phenyl)-ethyl]-carbamic acid benzyl ester (119372-44-0) → (S)-4-Benzyloxycarbonylamino-2,2-difluoro-3-hydroxy-5-(4-nitro-phenyl)-pentanoic acid ethyl ester (119372-54-2,119372-55-3,119920-86-4,138875-60-2,138875-61-3)

Guidance literature:

With zinc; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)82154-1

Reference yield: 30.0%

→ (R,S)-4-benzyloxycarbonylamino-5-(4-nitrophenyl)-2,2-difluoro-3-hydroxypentanoic acid ethyl ester (119920-86-4)

Guidance literature:

Reference yield:

(R,S)-α-benzyloxycarbonylamino-3-(4-nitrophenyl)propionic acid methyl ester (142035-73-2) → (R,S)-4-benzyloxycarbonylamino-5-(4-nitrophenyl)-2,2-difluoro-3-hydroxypentanoic acid ethyl ester (119920-86-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / ddisobutylaluminium hydride / diethyl ether; toluene; hexane / 0.17 h / -78 °C

2: 1.) zinc, iodine / 1.) THF, rt, 15 min, ultrasonication; 2.) THF, rt, 35 min, ultrasonication

With iodine; diisobutylaluminium hydride; zinc; In diethyl ether; hexane; toluene;

DOI:10.1016/0040-4020(95)00896-G

upstream raw materials:

Ethyl bromodifluoroacetate

[(S)-1-Formyl-2-(4-nitro-phenyl)-ethyl]-carbamic acid benzyl ester

(S)-2-Benzyloxycarbonylamino-3-(4-nitro-phenyl)-propionic acid methyl ester

(R,S)-α-benzyloxycarbonylamino-3-(4-nitrophenyl)propanal

Downstream raw materials:

C₅₂H₅₅F₂N₇O₁₀

(S)-1-((R)-2-Amino-3-phenyl-propionyl)-pyrrolidine-2-carboxylic acid [4-acetylamino-3,3-difluoro-1-(4-guanidino-benzyl)-2-oxo-butyl]-amide; hydrochloride

(N-benzyloxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-3,3-difluoro-2-hydroxy-1-<4((((benzyloxycarbonylamino)benzyloxycarbonylimino)methyl)amino)phenyl>methyl>butyl-L-prolinamide

(N-tert-butoxycarbonyl-D-phenylalanyl)-N-<4-acetylamino-1-<(4-tert-butoxycarbonylaminophenyl)methyl>-3,3-difluoro-2-hydroxybutyl>-L-prolinamide