Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester

Base Information

• Chemical Name: Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester
• CAS No.: 182414-61-5
• Molecular Formula: C₂₂H₂₂N₂O₉S
• Molecular Weight: 490.491
• Mol file: 182414-61-5.mol

Synonyms:Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester

Chemical Property of Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester

There total 6 articles about Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-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: 90.0%

allyl (5S,6S,1'R)-6-(1'-hydroxyethyl)penem-3-carboxylate (158250-71-6) + p-Nitrobenzyl monoester of succinic acid (79581-93-4) → Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester (182414-61-5)

Guidance literature:

With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; 1.) -15 deg C, 20 min, 2.) 0 deg C, 30 min;

DOI:10.7164/antibiotics.49.921

Reference yield:

allyl 2-oxoacetate (64370-42-9) → Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester (182414-61-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.) 2,6-lutidine, SOCl₂, 3.) 2,6-lutidine / 1.) benzene, reflux, 1 h, 2.) THF, -20 deg C to room temperature, 3.) dioxan, 40 deg C, 18 h

2: 1.) AgNO₃, pyridine, 2.) acetic formic anhydride, DMAP, Et₃NHCl / 1.) CH₂Cl₂, MeOH, 30 min, 2.) CH₂Cl₂, 0 deg C, 30 min

3: 45 percent / ethyl acetate / 0.5 h / Irradiation

4: 95 percent / TBAF / acetic acid; tetrahydrofuran / 7 h

5: 90 percent / DMAP, 1-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.) -15 deg C, 20 min, 2.) 0 deg C, 30 min

With pyridine; 2,6-dimethylpyridine; dmap; thionyl chloride; tetrabutyl ammonium fluoride; triethylamine hydrochloride; silver nitrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; formyl acetic anhydride; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate;

DOI:10.7164/antibiotics.49.921

Reference yield:

(3S,4R)-3-((R)-1-(t-butyldimethylsilyloxy)ethyl)-4-triphenylmethylthio-2-azetidinone (88035-31-8) → Succinic acid (R)-1-((5S,6S)-2-allyloxycarbonyl-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-en-6-yl)-ethyl ester 4-nitro-benzyl ester (182414-61-5)

Guidance literature:

Multi-step reaction with 5 steps

1: 2.) 2,6-lutidine, SOCl₂, 3.) 2,6-lutidine / 1.) benzene, reflux, 1 h, 2.) THF, -20 deg C to room temperature, 3.) dioxan, 40 deg C, 18 h

2: 1.) AgNO₃, pyridine, 2.) acetic formic anhydride, DMAP, Et₃NHCl / 1.) CH₂Cl₂, MeOH, 30 min, 2.) CH₂Cl₂, 0 deg C, 30 min

3: 45 percent / ethyl acetate / 0.5 h / Irradiation

4: 95 percent / TBAF / acetic acid; tetrahydrofuran / 7 h

5: 90 percent / DMAP, 1-dimethylaminopropyl-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 1.) -15 deg C, 20 min, 2.) 0 deg C, 30 min

With pyridine; 2,6-dimethylpyridine; dmap; thionyl chloride; tetrabutyl ammonium fluoride; triethylamine hydrochloride; silver nitrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; formyl acetic anhydride; In tetrahydrofuran; dichloromethane; acetic acid; ethyl acetate;

DOI:10.7164/antibiotics.49.921

upstream raw materials:

allyl (5S,6S,1'R)-6-(1'-hydroxyethyl)penem-3-carboxylate

p-Nitrobenzyl monoester of succinic acid

allyl 2-oxoacetate

(3S,4R)-3-((R)-1-(t-butyldimethylsilyloxy)ethyl)-4-triphenylmethylthio-2-azetidinone

Refernces