1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-(acetylamino)ethyl]thio]-7-oxo-6-(tetrahydro-3-hydroxy-3-thienyl)-, (4-nitrophenyl)methyl ester, S,S-dioxide

Base Information

Chemical Name:1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-(acetylamino)ethyl]thio]-7-oxo-6-(tetrahydro-3-hydroxy-3-thienyl)-, (4-nitrophenyl)methyl ester, S,S-dioxide
CAS No.:98811-20-2
Molecular Formula:C₂₂H₂₅N₃O₉S₂
Molecular Weight:539.587
Hs Code.:

1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid,
3-[[2-(acetylamino)ethyl]thio]-7-oxo-6-(tetrahydro-3-hydroxy-3-thienyl)-,
(4-nitrophenyl)methyl ester, S,S-dioxide

Synonyms:

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Chemical Property of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-(acetylamino)ethyl]thio]-7-oxo-6-(tetrahydro-3-hydroxy-3-thienyl)-, (4-nitrophenyl)methyl ester, S,S-dioxide

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Technology Process of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-(acetylamino)ethyl]thio]-7-oxo-6-(tetrahydro-3-hydroxy-3-thienyl)-, (4-nitrophenyl)methyl ester, S,S-dioxide

There total 9 articles about 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-(acetylamino)ethyl]thio]-7-oxo-6-(tetrahydro-3-hydroxy-3-thienyl)-, (4-nitrophenyl)methyl ester, S,S-dioxide 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:

: 98827-07-7
7-(1-hydroxy-3-thiacyclopentyl)-7-phenylthio-8-oxo-2,2-dimethyl-3-oxa-1-azabicyclo[4.2.0]octane

: 98811-20-2
(5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(3-hydroxy-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 80 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: 90 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile

7: titanium tetrachloride / CH₂Cl₂ / 1 h / 0 °C

8: rhodium(II) diacetate / tetrahydrofuran; benzene / 0.12 h / 80 °C

9: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile, 1.5 h, 0 deg C; 2.) acetonitirile, 1 h, 0 deg C

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

Reference yield:

: 98810-66-3
{(2R,3R)-3-[3-(2-Methoxy-ethoxymethoxy)-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl]-4-oxo-azetidin-2-yl}-acetic acid

: 98811-20-2
(5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(3-hydroxy-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

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

2: 90 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile

3: titanium tetrachloride / CH₂Cl₂ / 1 h / 0 °C

4: rhodium(II) diacetate / tetrahydrofuran; benzene / 0.12 h / 80 °C

5: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile, 1.5 h, 0 deg C; 2.) acetonitirile, 1 h, 0 deg C

With 4-toluenesulfonyl azide; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; rhodium(II) acetate; In tetrahydrofuran; dichloromethane; acetonitrile; benzene;
DOI:10.1248/cpb.35.996

Reference yield:

: 98810-65-2
(6R,7R)-7-[3-(2-Methoxy-ethoxymethoxy)-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl]-2,2-dimethyl-3-oxa-1-aza-bicyclo[4.2.0]octan-8-one

: 98811-20-2
(5S,6S)-3-(2-Acetylamino-ethylsulfanyl)-6-(3-hydroxy-1,1-dioxo-tetrahydro-1λ⁶-thiophen-3-yl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 8 N Jones reagent / acetone

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

3: 90 percent / p-toluenesulfonyl azide, triethylamine / acetonitrile

4: titanium tetrachloride / CH₂Cl₂ / 1 h / 0 °C

5: rhodium(II) diacetate / tetrahydrofuran; benzene / 0.12 h / 80 °C

6: 1.) diisopropylethylamine, diphenyl chlorophosphate; 2.) diisopropylethylamine / 1.) acetonitrile, 1.5 h, 0 deg C; 2.) acetonitirile, 1 h, 0 deg C

With 4-toluenesulfonyl azide; jones reagent; titanium tetrachloride; triethylamine; N-ethyl-N,N-diisopropylamine; chlorophosphoric acid diphenyl ester; 1,1'-carbonyldiimidazole; rhodium(II) acetate; In tetrahydrofuran; dichloromethane; acetone; acetonitrile; benzene;
DOI:10.1248/cpb.35.996