1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[(diethylamino)carbonyl]phenyl]thio]-6-[(1R)-1-[[(1,1-dimethylethyl) dimethylsilyl]oxy]ethyl]-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, (4R,5S,6S)-

Base Information

• Chemical Name: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[(diethylamino)carbonyl]phenyl]thio]-6-[(1R)-1-[[(1,1-dimethylethyl) dimethylsilyl]oxy]ethyl]-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, (4R,5S,6S)-
• CAS No.: 158168-59-3
• Molecular Formula: C34H45N3O7SSi
• Molecular Weight: 667.899
• Mol file: 158168-59-3.mol

Synonyms:

Chemical Property of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[(diethylamino)carbonyl]phenyl]thio]-6-[(1R)-1-[[(1,1-dimethylethyl) dimethylsilyl]oxy]ethyl]-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, (4R,5S,6S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[(diethylamino)carbonyl]phenyl]thio]-6-[(1R)-1-[[(1,1-dimethylethyl) dimethylsilyl]oxy]ethyl]-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, (4R,5S,6S)-

There total 9 articles about 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[[2-[(diethylamino)carbonyl]phenyl]thio]-6-[(1R)-1-[[(1,1-dimethylethyl) dimethylsilyl]oxy]ethyl]-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester, (4R,5S,6S)- 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: 28.0%

thiophenol (108-98-5) + (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-benzenesulfinyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (158168-62-8) → (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (105344-46-5) + (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-phenylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (158168-59-3)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; magnesium bromide; In tetrahydrofuran; for 0.666667h; Ambient temperature;

DOI:10.1016/S0040-4039(97)01239-2

Reference yield:

2,2'-disulfanediylbis(N,N-diethylbenzamide) (49755-52-4) → (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-phenylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (158168-59-3)

Guidance literature:

Multi-step reaction with 5 steps

1: 96 percent / Zn / benzene / 3.33 h / Heating

2: lithium bis(trimethylsilyl)amide, DMF / tetrahydrofuran / 0.5 h / -78 - -65 °C

3: ZnCl₂ / CH₂Cl₂ / 2.33 h / Heating

4: triethylamine / CH₂Cl₂ / 0.25 h

5: 1.) dipropyl ethylphosphonite / 1.) RT, 150 min, 2.) xylene, reflux, 6 h

With dipropyl ethylphosphonite; triethylamine; N,N-dimethyl-formamide; zinc(II) chloride; lithium hexamethyldisilazane; zinc; In tetrahydrofuran; dichloromethane; benzene;

DOI:10.1248/cpb.45.1439

Reference yield:

(3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one (76899-07-5,78963-47-0,78963-48-1,78963-60-7,80951-41-3,81275-02-7,85647-75-2,85954-95-6,92217-74-8,104527-11-9,76855-69-1) → (4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-phenylsulfanyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester (158168-59-3)

Guidance literature:

Multi-step reaction with 3 steps

1: ZnCl₂ / CH₂Cl₂ / 2 h / Ambient temperature

2: triethylamine / CH₂Cl₂ / 0.25 h

3: 1.) dipropyl ethylphosphonite / 1.) RT, 150 min, 2.) xylene, reflux, 6 h

With dipropyl ethylphosphonite; triethylamine; zinc(II) chloride; In dichloromethane;

DOI:10.1248/cpb.45.1439

upstream raw materials:

{(2S,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-2-[(R)-1-(2-diethylcarbamoyl-phenylsulfanylcarbonyl)-ethyl]-4-oxo-azetidin-1-yl}-oxo-acetic acid 4-nitro-benzyl ester

thiophenol

(4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-benzenesulfinyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

chloroxoacetic acid (4-nitrophenyl)methyl ester

Downstream raw materials:

(4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-benzenesulfinyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-3-(2-diethylcarbamoyl-benzenesulfonyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4R,5S,6S)-6-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-3-phenylsulfanyl-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

(4R,5S,6S)-3-Benzylsulfanyl-6-[(R)-1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester