(2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane

Base Information

• Chemical Name: (2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane
• CAS No.: 216861-01-7
• Molecular Formula: C₁₇H₂₀N₂O₆
• Molecular Weight: 348.356

Synonyms:(2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane

Chemical Property of (2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane

There total 27 articles about (2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane 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:

(R)-6-Hydroxy-5-<(phenylsulfonyl)amino>-1-hexen-4-one (150989-63-2) → (2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane (216861-01-7)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 84 percent / L-Selectride / tetrahydrofuran / 2.25 h / -78 - -73 °C

2.1: 80 percent / p-toluenesulfonic acid / tetrahydrofuran / 48 h / 20 °C

3.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

3.2: 81 percent / NaOH; H₂O₂ / tetrahydrofuran; ethanol; H₂O / 0 - 20 °C / Heating

4.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

5.1: KHMDS / toluene; tetrahydrofuran / 6.25 h / -78 - 0 °C

5.2: toluene; tetrahydrofuran / 17.5 h / -78 - 0 °C

6.1: 68 percent / NaH / 1,2-dimethoxy-ethane / 144 h / 20 °C

7.1: conc. HCl / methanol / 14 h / 20 °C

8.1: 0.62 g / 2,6-lutidine / CH₂Cl₂ / 2 h / -10 °C

9.1: 86 percent / tetraethylammonium bromide; 4-phenylphenol / acetonitrile / 26 h / Electrolysis

10.1: 99 percent / LiOH*H₂O / methanol; H₂O / 12 h / 0 - 20 °C

11.1: 90 percent / 2-chloro-1-methylpyridinium triflate; N,N-diisopropylethylamine / acetonitrile / 16.25 h / 20 - 70 °C

12.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

12.2: 88 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

13.1: 96 percent / p-TsOH / tetrahydrofuran; H₂O / 37.5 h / 20 °C

14.1: 110 mg / NaIO₄ / RuCl₃*3H₂O / acetonitrile; CCl₄; H₂O / 3 h / 20 °C

15.1: 80 mg / TBAF / tetrahydrofuran / 18 h / 20 °C

16.1: 80 mg / N,N-diisopropylethylamine / dimethylformamide / 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 4-Phenylphenol; tetraethylammonium bromide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; L-Selectride; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; N-methyl-2-chloropyridinium trifluoromethanesulfonate; ruthenium trichloride; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Reduction / 2.1: Cyclization / 3.1: Addition / 3.2: Oxidation / 4.1: Oxidation / 5.1: Metallation / 5.2: Condensation / 6.1: Cyclization / 7.1: Hydrolysis / 8.1: silylation / 9.1: Reduction / 10.1: Hydrolysis / 11.1: Cyclization / 12.1: Metallation / 12.2: Alkylation / 13.1: Hydrolysis / 14.1: Oxidation / 15.1: desilylation / 16.1: Esterification;

DOI:10.1021/jo980592s

Reference yield:

(4R/S,5R)-5-[(phenylsulfonyl)amino]-4,6-dihydroxy-2-hexene → (2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane (216861-01-7)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 80 percent / p-toluenesulfonic acid / tetrahydrofuran / 48 h / 20 °C

2.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

2.2: 81 percent / NaOH; H₂O₂ / tetrahydrofuran; ethanol; H₂O / 0 - 20 °C / Heating

3.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

4.1: KHMDS / toluene; tetrahydrofuran / 6.25 h / -78 - 0 °C

4.2: toluene; tetrahydrofuran / 17.5 h / -78 - 0 °C

5.1: 68 percent / NaH / 1,2-dimethoxy-ethane / 144 h / 20 °C

6.1: conc. HCl / methanol / 14 h / 20 °C

7.1: 0.62 g / 2,6-lutidine / CH₂Cl₂ / 2 h / -10 °C

8.1: 86 percent / tetraethylammonium bromide; 4-phenylphenol / acetonitrile / 26 h / Electrolysis

9.1: 99 percent / LiOH*H₂O / methanol; H₂O / 12 h / 0 - 20 °C

10.1: 90 percent / 2-chloro-1-methylpyridinium triflate; N,N-diisopropylethylamine / acetonitrile / 16.25 h / 20 - 70 °C

11.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

11.2: 88 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

12.1: 96 percent / p-TsOH / tetrahydrofuran; H₂O / 37.5 h / 20 °C

13.1: 110 mg / NaIO₄ / RuCl₃*3H₂O / acetonitrile; CCl₄; H₂O / 3 h / 20 °C

14.1: 80 mg / TBAF / tetrahydrofuran / 18 h / 20 °C

15.1: 80 mg / N,N-diisopropylethylamine / dimethylformamide / 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 4-Phenylphenol; tetraethylammonium bromide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; N-methyl-2-chloropyridinium trifluoromethanesulfonate; ruthenium trichloride; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Cyclization / 2.1: Addition / 2.2: Oxidation / 3.1: Oxidation / 4.1: Metallation / 4.2: Condensation / 5.1: Cyclization / 6.1: Hydrolysis / 7.1: silylation / 8.1: Reduction / 9.1: Hydrolysis / 10.1: Cyclization / 11.1: Metallation / 11.2: Alkylation / 12.1: Hydrolysis / 13.1: Oxidation / 14.1: desilylation / 15.1: Esterification;

DOI:10.1021/jo980592s

Reference yield:

(4R,5R)-4-Allyl-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane (150989-66-5) → (2S,3R,6R,7R)-2-(p-nitrobenzyloxycarbonyl)-7-ethyl-8-oxo-3-hydroxy-1-azabicyclo[4.2.0]octane (216861-01-7)

Guidance literature:

Multi-step reaction with 14 steps

1.1: 9-BBN / tetrahydrofuran / 4 h / 20 °C

1.2: 81 percent / NaOH; H₂O₂ / tetrahydrofuran; ethanol; H₂O / 0 - 20 °C / Heating

2.1: Dess-Martin periodinane; pyridine / CH₂Cl₂ / 2 h / 20 °C

3.1: KHMDS / toluene; tetrahydrofuran / 6.25 h / -78 - 0 °C

3.2: toluene; tetrahydrofuran / 17.5 h / -78 - 0 °C

4.1: 68 percent / NaH / 1,2-dimethoxy-ethane / 144 h / 20 °C

5.1: conc. HCl / methanol / 14 h / 20 °C

6.1: 0.62 g / 2,6-lutidine / CH₂Cl₂ / 2 h / -10 °C

7.1: 86 percent / tetraethylammonium bromide; 4-phenylphenol / acetonitrile / 26 h / Electrolysis

8.1: 99 percent / LiOH*H₂O / methanol; H₂O / 12 h / 0 - 20 °C

9.1: 90 percent / 2-chloro-1-methylpyridinium triflate; N,N-diisopropylethylamine / acetonitrile / 16.25 h / 20 - 70 °C

10.1: diisopropylamine; n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

10.2: 88 percent / tetrahydrofuran; hexane / 3.5 h / -78 °C

11.1: 96 percent / p-TsOH / tetrahydrofuran; H₂O / 37.5 h / 20 °C

12.1: 110 mg / NaIO₄ / RuCl₃*3H₂O / acetonitrile; CCl₄; H₂O / 3 h / 20 °C

13.1: 80 mg / TBAF / tetrahydrofuran / 18 h / 20 °C

14.1: 80 mg / N,N-diisopropylethylamine / dimethylformamide / 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; lithium hydroxide; sodium periodate; 9-borabicyclo[3.3.1]nonane dimer; n-butyllithium; 4-Phenylphenol; tetraethylammonium bromide; tetrabutyl ammonium fluoride; potassium hexamethylsilazane; sodium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; diisopropylamine; N-ethyl-N,N-diisopropylamine; N-methyl-2-chloropyridinium trifluoromethanesulfonate; ruthenium trichloride; In tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; acetonitrile; 1.1: Addition / 1.2: Oxidation / 2.1: Oxidation / 3.1: Metallation / 3.2: Condensation / 4.1: Cyclization / 5.1: Hydrolysis / 6.1: silylation / 7.1: Reduction / 8.1: Hydrolysis / 9.1: Cyclization / 10.1: Metallation / 10.2: Alkylation / 11.1: Hydrolysis / 12.1: Oxidation / 13.1: desilylation / 14.1: Esterification;

DOI:10.1021/jo980592s

upstream raw materials:

1-bromomethyl-4-nitro-benzene

(2S,3R,6R,7R)-2-carboxyl-7-ethyl-3-hydroxy-8-oxo-1-azabicyclo[4.2.0]octane

(R)-6-Hydroxy-5-<(phenylsulfonyl)amino>-1-hexen-4-one

(4R,5R)-4-(3-Hydroxypropyl)-2,2-dimethyl-5-<(phenylsulfonyl)amino>-1,3-dioxane

Downstream raw materials:

(6R,7R)-7-Ethyl-3-hydroxy-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-nitro-benzyl ester

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