(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

Base Information

Chemical Name:(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
CAS No.:87096-01-3
Molecular Formula:C₃₁H₂₂N₄O₁₁S
Molecular Weight:658.602
Hs Code.:

(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

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Chemical Property of (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

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Technology Process of (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

There total 12 articles about (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 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: 21.4%

: 100163-38-0
(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

: 87096-01-3
(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

Guidance literature:: In toluene; for 2h; Heating;
DOI:10.1021/jo00355a011

Reference yield:

: 59034-26-3
(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

: 87096-01-3
(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

Guidance literature:: Multi-step reaction with 9 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

8: 79.6 percent / perchloric acid / CH₂Cl₂ / 0.67 h / Ambient temperature

9: 21.4 percent / toluene / 2 h / Heating

With 2,6-dimethylpyridine; dirhodium tetraacetate; potassium permanganate; thionyl chloride; perchloric acid; 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:

: 82551-63-1
4-nitrobenzyl 2-diazo-3-oxo-butanoate

: 87096-01-3
(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

Guidance literature:: Multi-step reaction with 9 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

8: 79.6 percent / perchloric acid / CH₂Cl₂ / 0.67 h / Ambient temperature

9: 21.4 percent / toluene / 2 h / Heating

With 2,6-dimethylpyridine; dirhodium tetraacetate; potassium permanganate; thionyl chloride; perchloric acid; 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