(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone

Base Information

• Chemical Name: (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone
• CAS No.: 263020-24-2
• Molecular Formula: C₂₇H₃₇N₃O₉SSi
• Molecular Weight: 607.757
• Mol file: 263020-24-2.mol

Synonyms:

Chemical Property of (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone

There total 3 articles about (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone 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:

chloroxoacetic acid (4-nitrophenyl)methyl ester (81779-73-9) + (R)-2-{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-((R)-5-oxo-1-trimethylsilanyl-pyrrolidin-3-yl) ester → (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone (263020-24-2)

Guidance literature:

With triethylamine; In dichloromethane; at -20 ℃; for 0.333333h;

DOI:10.1248/cpb.48.126

Reference yield:

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid (93711-85-4,97101-07-0,113033-46-8,120710-59-0,120710-60-3,90776-58-2) → (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone (263020-24-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: CDI / acetonitrile / 1 h / 20 °C

1.2: 86 percent / acetonitrile / 15 h / 20 °C

2.1: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

3.1: Et₃N / CH₂Cl₂ / 0.33 h / -20 °C

With triethylamine; 1,1'-carbonyldiimidazole; In dichloromethane; acetonitrile; 1.1: Condensation / 1.2: Condensation / 2.1: Silylation / 3.1: oxalylation;

DOI:10.1248/cpb.48.126

Reference yield:

(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone (176179-66-1) → (3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-1-[[(p-nitrobenzyl)oxy]oxalyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone (263020-24-2)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 0.17 h / 0 °C

2: Et₃N / CH₂Cl₂ / 0.33 h / -20 °C

With triethylamine; In dichloromethane; 1: Silylation / 2: oxalylation;

DOI:10.1248/cpb.48.126

upstream raw materials:

chloroxoacetic acid (4-nitrophenyl)methyl ester

(2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid

(3S,4S)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-[(R)-1-[[(R)-2-oxopyrrolidin-4-ylthio]carbonyl]ethyl]-2-azetidinone

Downstream raw materials:

C₃₃H₅₂N₃O₁₀PSSi

C₃₃H₅₂N₃O₁₁PSSi