{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: {(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester
• CAS No.: 87095-95-2
• Molecular Formula: C₃₃H₂₈N₄O₁₄S
• Molecular Weight: 736.67
• Mol file: 87095-95-2.mol

Synonyms:{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester

Chemical Property of {(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of {(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester

There total 8 articles about {(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 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: 79.5%

p-nitrobenzyl glyoxylate (64370-35-0) + [(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-ylsulfanyl]-(2-methyl-[1,3]dioxolan-2-yl)-acetic acid 4-nitro-benzyl ester (87095-94-1,100163-36-8,100163-37-9) → {(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester (87095-95-2)

Guidance literature:

With 3 A molecular sieve; In N,N-dimethyl-formamide; toluene; for 24h; Ambient temperature;

DOI:10.1021/jo00355a011

Reference yield:

(2S,5R,6R)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (59034-26-3) → {(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester (87095-95-2)

Guidance literature:

Multi-step reaction with 5 steps

1: Rh₂(OAc)4 / benzene; CH₂Cl₂ / 16 h / Heating

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: 30 percent / p-toluenesulfonic acid / benzene / 48 h / Heating

4: 68 percent / KMnO₄ / dimethylformamide; pyridine; H₂O / 5 h / 0 °C

5: 79.5 percent / 3-Angstroem 1/16 molecular sieves / dimethylformamide; toluene / 24 h / Ambient temperature

With dirhodium tetraacetate; potassium permanganate; 3 A molecular sieve; toluene-4-sulfonic acid; triethylamine; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00355a011

Reference yield:

4-nitrobenzyl 2-diazo-3-oxo-butanoate (82551-63-1) → {(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-hydroxy-acetic acid 4-nitro-benzyl ester (87095-95-2)

Guidance literature:

Multi-step reaction with 5 steps

1: Rh₂(OAc)4 / benzene; CH₂Cl₂ / 16 h / Heating

2: Et₃N / CH₂Cl₂ / 2 h / 0 °C

3: 30 percent / p-toluenesulfonic acid / benzene / 48 h / Heating

4: 68 percent / KMnO₄ / dimethylformamide; pyridine; H₂O / 5 h / 0 °C

5: 79.5 percent / 3-Angstroem 1/16 molecular sieves / dimethylformamide; toluene / 24 h / Ambient temperature

With dirhodium tetraacetate; potassium permanganate; 3 A molecular sieve; toluene-4-sulfonic acid; triethylamine; In pyridine; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00355a011

upstream raw materials:

p-nitrobenzyl glyoxylate

[(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-4-oxo-azetidin-2-ylsulfanyl]-(2-methyl-[1,3]dioxolan-2-yl)-acetic acid 4-nitro-benzyl ester

(2S,5R,6R)-benzyl 6-(1,3-dioxoisoindolin-2-yl)-3,3-dimethyl-7-oxo-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

4-nitrobenzyl 2-diazo-3-oxo-butanoate

Downstream raw materials:

Chloro-{(2R,3R)-3-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-[(2-methyl-[1,3]dioxolan-2-yl)-(4-nitro-benzyloxycarbonyl)-methylsulfanyl]-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester

(5R,6R)-6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-7-oxo-4-thia-1-aza-bicyclo[3.2.0]hept-2-ene-2,3-dicarboxylic acid bis-(4-nitro-benzyl) ester

(6R,7R)-7-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-3-methyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,4-dicarboxylic acid bis-(4-nitro-benzyl) ester

[(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-2-(4-nitro-benzyloxyoxalylsulfanyl)-4-oxo-azetidin-1-yl]-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester