{(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}-(triphenyl-λ⁵-phosphanylidene)-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}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester
• CAS No.: 87095-97-4
• Molecular Formula: C₅₁H₄₁N₄O₁₃PS
• Molecular Weight: 980.945
• Mol file: 87095-97-4.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}-(triphenyl-λ⁵-phosphanylidene)-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}-(triphenyl-λ⁵-phosphanylidene)-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}-(triphenyl-λ⁵-phosphanylidene)-acetic acid 4-nitro-benzyl ester

There total 10 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}-(triphenyl-λ⁵-phosphanylidene)-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:

(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}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (87095-97-4)

Guidance literature:

Multi-step reaction with 7 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

6: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.33 h / Ambient temperature

7: 2,6-lutidine / dioxane / 36 h / Ambient temperature

With 2,6-dimethylpyridine; dirhodium tetraacetate; potassium permanganate; thionyl chloride; 3 A molecular sieve; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; 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}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (87095-97-4)

Guidance literature:

Multi-step reaction with 7 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

6: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.33 h / Ambient temperature

7: 2,6-lutidine / dioxane / 36 h / Ambient temperature

With 2,6-dimethylpyridine; dirhodium tetraacetate; potassium permanganate; thionyl chloride; 3 A molecular sieve; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; pyridine; dichloromethane; water; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/jo00355a011

Reference yield:

[(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}-(triphenyl-λ5-phosphanylidene)-acetic acid 4-nitro-benzyl ester (87095-97-4)

Guidance literature:

Multi-step reaction with 3 steps

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

2: 2,6-lutidine, thionyl chloride / tetrahydrofuran / 0.33 h / Ambient temperature

3: 2,6-lutidine / dioxane / 36 h / Ambient temperature

With 2,6-dimethylpyridine; thionyl chloride; 3 A molecular sieve; In tetrahydrofuran; 1,4-dioxane; N,N-dimethyl-formamide; toluene;

DOI:10.1021/jo00355a011

upstream 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

triphenylphosphine

(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:

(Z)-2-{(2R,3R)-3-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-1-[(4-nitro-benzyloxycarbonyl)-(triphenyl-λ⁵-phosphanylidene)-methyl]-4-oxo-azetidin-2-ylsulfanyl}-3-hydroxy-but-2-enoic 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

Refernces

• 1、 Kametani, Tetsuji,Kanaya, Naoaki,Mochizuki, Tomoko,,Honda, Toshio. "NOVEL TRANSFORMATION OF PENICILLIN INTO PENEM NUCLEUS : SYNTHESIS OF 2-CARBOXYLPENEM DERIVATIVE". . p. 1511 - 1512. Retrieved 2007/10/02.