Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 4-nitro-benzyl ester

Base Information

• Chemical Name: Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 4-nitro-benzyl ester
• CAS No.: 88670-08-0
• Molecular Formula: C₂₂H₂₆N₈O₇S
• Molecular Weight: 546.564

Synonyms:Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 4-nitro-benzyl ester

Chemical Property of Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 4-nitro-benzyl ester

Chemical Property:

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Technology Process of Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 4-nitro-benzyl ester

There total 10 articles about Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 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:

((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl chloride (50780-46-6) → Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 4-nitro-benzyl ester (88670-08-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 37 percent / triethylamine / acetonitrile / 1.) r.t., 16 h; 2.) 60 deg C, 1 h

2: 1.) lithium triethylcarboxide / 1.) THF, hexane, -78 deg C, 10 min; 2.) dichloromethane, dimethylformamide, -78 deg C, 45 min

3: trifluoroacetic acid / CH₂Cl₂ / 6 h / Ambient temperature

4: 0.72 g / hydrofluoric acid / acetonitrile / 18 h / -10 °C

5: 0.302 g / p-dodecylbenzenesulfonylazide, triethylamine / hexane; CH₂Cl₂ / 1 h / -15 °C

6: 89 percent / rhodium acetate dimer / CH₂Cl₂ / 1 h / Heating

7: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 0.67 h / -78 °C

8: 1.) NaSH, i-Pr₂NEt / 1.) DMF

With dirhodium tetraacetate; sodium hydrogensulfide; hydrogen fluoride; lithium 3-ethylpentan-3-olate; 4-dodecylbenzenesulphonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ja00318a042

Reference yield:

(3S,4R)-1-tert-butyldimethylsilyl-3-<(R)-2-((tert-butyldimethylsilyl)oxy)ethyl>-2-oxo-azetidin-4-acetic acid (88670-04-6) → Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 4-nitro-benzyl ester (88670-08-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) sodium carbonate; 2.) oxalyl chloride / 1.) THF, acetonitrile, 50 deg C, 1 h; 2.) dichloromethane, dimethylformamide, -15 deg C

2: 1.) lithium triethylcarboxide / 1.) THF, hexane, -78 deg C, 10 min; 2.) dichloromethane, dimethylformamide, -78 deg C, 45 min

3: trifluoroacetic acid / CH₂Cl₂ / 6 h / Ambient temperature

4: 0.72 g / hydrofluoric acid / acetonitrile / 18 h / -10 °C

5: 0.302 g / p-dodecylbenzenesulfonylazide, triethylamine / hexane; CH₂Cl₂ / 1 h / -15 °C

6: 89 percent / rhodium acetate dimer / CH₂Cl₂ / 1 h / Heating

7: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 0.67 h / -78 °C

8: 1.) NaSH, i-Pr₂NEt / 1.) DMF

With dirhodium tetraacetate; sodium hydrogensulfide; oxalyl dichloride; hydrogen fluoride; lithium 3-ethylpentan-3-olate; sodium carbonate; 4-dodecylbenzenesulphonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ja00318a042

Reference yield:

(3S,4R)-1-(tert-butyldimethylsilyl)-3-<(R)-1-((tert-butyldimethylsilyl)oxy)ethyl>azetidin-2-one-4-acetyl chloride (88728-84-1) → Carbonic acid 5-[(5R,6S)-3-(N,N-dimethyl-carbamimidoylmethylsulfanyl)-6-((R)-1-hydroxy-ethyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-2-yl]-tetrazol-1-ylmethyl ester 4-nitro-benzyl ester (88670-08-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) lithium triethylcarboxide / 1.) THF, hexane, -78 deg C, 10 min; 2.) dichloromethane, dimethylformamide, -78 deg C, 45 min

2: trifluoroacetic acid / CH₂Cl₂ / 6 h / Ambient temperature

3: 0.72 g / hydrofluoric acid / acetonitrile / 18 h / -10 °C

4: 0.302 g / p-dodecylbenzenesulfonylazide, triethylamine / hexane; CH₂Cl₂ / 1 h / -15 °C

5: 89 percent / rhodium acetate dimer / CH₂Cl₂ / 1 h / Heating

6: 1,8-diazabicyclo<5.4.0>undec-7-ene / tetrahydrofuran / 0.67 h / -78 °C

7: 1.) NaSH, i-Pr₂NEt / 1.) DMF

With dirhodium tetraacetate; sodium hydrogensulfide; hydrogen fluoride; lithium 3-ethylpentan-3-olate; 4-dodecylbenzenesulphonyl azide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; hexane; dichloromethane; acetonitrile;

DOI:10.1021/ja00318a042

upstream raw materials:

N,N-dimethylchloroacetamidine

Trifluoro-methanesulfonic acid (5R,6S)-6-((R)-1-hydroxy-ethyl)-2-[1-(4-nitro-benzyloxycarbonyloxymethyl)-1H-tetrazol-5-yl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-en-3-yl ester

((((p-nitrobenzyl)oxy)carbonyl)oxy)methyl chloride

(3S,4R)-1-(tert-butyldimethylsilyl)-3-<(R)-1-((tert-butyldimethylsilyl)oxy)ethyl>azetidin-2-one-4-acetyl chloride

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