(5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-4-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-4-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 98811-27-9
• Molecular Formula: C₂₃H₂₇N₃O₉S₂
• Molecular Weight: 553.614

Synonyms:

Chemical Property of (5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-4-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-4-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

There total 11 articles about (5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(4-hydroxy-1,1-dioxo-hexahydro-1λ⁶-thiopyran-4-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic 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:

Tetrahydrothiopyran-4-one (1072-72-6) → (5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(4-hydroxy-1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (98811-27-9,115995-82-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 1.) lithium aluminum hydride / 1.) THF; 2.) THF

2: 64 percent / azobisisobutyronitrile, triphenyltin hydride / acetone

3: diisopropylethylamine / CH₂Cl₂

4: 70 percent m-chloroperbenzoic acid / CH₂Cl₂

5: 8 N Jones reagent / acetone

6: 1.) N,N-carbonyldiimidazole / 1.) THF; 2.) THF

7: 98 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile

8: titanium tetrachloride / CH₂Cl₂

9: rhodium(II) diacetate / tetrahydrofuran; benzene

10: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile; 2.) acetonitirile

With lithium aluminium tetrahydride; 4-toluenesulfonyl azide; jones reagent; 2,2'-azobis(isobutyronitrile); triphenylstannane; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; rhodium(II) acetate; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; benzene;

DOI:10.1248/cpb.35.996

Reference yield:

(6R,7R)-7-[4-(2-Methoxy-ethoxymethoxy)-tetrahydro-thiopyran-4-yl]-2,2-dimethyl-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one (98810-74-3,115995-78-3) → (5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(4-hydroxy-1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (98811-27-9,115995-82-9)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent m-chloroperbenzoic acid / CH₂Cl₂

2: 8 N Jones reagent / acetone

3: 1.) N,N-carbonyldiimidazole / 1.) THF; 2.) THF

4: 98 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile

5: titanium tetrachloride / CH₂Cl₂

6: rhodium(II) diacetate / tetrahydrofuran; benzene

7: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile; 2.) acetonitirile

With 4-toluenesulfonyl azide; jones reagent; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; rhodium(II) acetate; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; benzene;

DOI:10.1248/cpb.35.996

Reference yield:

7-(1-hydroxy-4-thiacyclohexyl)-7-phenylthio-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane (98810-72-1) → (5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(4-hydroxy-1,1-dioxo-hexahydro-1λ6-thiopyran-4-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (98811-27-9,115995-82-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 64 percent / azobisisobutyronitrile, triphenyltin hydride / acetone

2: diisopropylethylamine / CH₂Cl₂

3: 70 percent m-chloroperbenzoic acid / CH₂Cl₂

4: 8 N Jones reagent / acetone

5: 1.) N,N-carbonyldiimidazole / 1.) THF; 2.) THF

6: 98 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile

7: titanium tetrachloride / CH₂Cl₂

8: rhodium(II) diacetate / tetrahydrofuran; benzene

9: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile; 2.) acetonitirile

With 4-toluenesulfonyl azide; jones reagent; 2,2'-azobis(isobutyronitrile); triphenylstannane; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; rhodium(II) acetate; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; benzene;

DOI:10.1248/cpb.35.996

upstream raw materials:

2-(acetylamino)ethanethiol

Tetrahydrothiopyran-4-one

(6R,7R)-7-[4-(2-Methoxy-ethoxymethoxy)-tetrahydro-thiopyran-4-yl]-2,2-dimethyl-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one

7-(1-hydroxy-4-thiacyclohexyl)-7-phenylthio-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane

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