(S)-3-{2-[(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: (S)-3-{2-[(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester
• CAS No.: 90629-08-6
• Molecular Formula: C₃₆H₃₃N₅O₁₆S
• Molecular Weight: 823.748

Synonyms:

Chemical Property of (S)-3-{2-[(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-3-{2-[(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

There total 7 articles about (S)-3-{2-[(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-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:

<3S-<3α(S*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate (87392-18-5) → (S)-3-{2-[(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (90629-08-6)

Guidance literature:

Multi-step reaction with 5 steps

1: 100 percent / H₂ / 10percent Pd-C / methanol

2: N,N'-dicyclohexylcarbodiimide / 4-(N,N-dimethylamino)pyridine / benzene

3: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

4: 61 percent / DMAP / CH₂Cl₂

5: Et₃N / CH₂Cl₂ / 0 °C

With dmap; boron trifluoride diethyl etherate; hydrogen; triethylamine; dicyclohexyl-carbodiimide; dmap; palladium on activated charcoal; In methanol; dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0040-4039(01)81292-2

Reference yield:

{(2R,3S)-3-[(R)-1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl}-acetic acid benzyl ester → (S)-3-{2-[(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (90629-08-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / pyridinium p-toluenesulfonate / tetrahydrofuran; H₂O / 0.5 h / Ambient temperature

2: 100 percent / H₂ / 10percent Pd-C / methanol

3: N,N'-dicyclohexylcarbodiimide / 4-(N,N-dimethylamino)pyridine / benzene

4: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

5: 61 percent / DMAP / CH₂Cl₂

6: Et₃N / CH₂Cl₂ / 0 °C

With dmap; boron trifluoride diethyl etherate; hydrogen; triethylamine; dicyclohexyl-carbodiimide; dmap; palladium on activated charcoal; pyridinium p-toluenesulfonate; In tetrahydrofuran; methanol; dichloromethane; water; acetonitrile; benzene;

DOI:10.1016/S0040-4039(01)81292-2

Reference yield:

(3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-(carboxymethyl)azetidin-2-one (88669-70-9) → (S)-3-{2-[(2R,3S)-3-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-1-(4-nitro-benzyloxyoxalyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester (90629-08-6)

Guidance literature:

Multi-step reaction with 4 steps

1: N,N'-dicyclohexylcarbodiimide / 4-(N,N-dimethylamino)pyridine / benzene

2: boron trifluoride etherate / acetonitrile / 0.5 h / 0 °C

3: 61 percent / DMAP / CH₂Cl₂

4: Et₃N / CH₂Cl₂ / 0 °C

With dmap; boron trifluoride diethyl etherate; triethylamine; dicyclohexyl-carbodiimide; dmap; In dichloromethane; acetonitrile; benzene;

DOI:10.1016/S0040-4039(01)81292-2

upstream raw materials:

chloroxoacetic acid (4-nitrophenyl)methyl ester

(3S,4R)-3-[(R)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-([(S)-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio]carbonylmethyl)-2-azetidinone

<3S-<3α(S^*),4β>>-benzyl<3-(1-t-butyldimethylsilyloxyethyl)-2-azetidinone-4-yl>acetate

(S)-3-{2-[(2R,3S)-3-((R)-1-Hydroxy-ethyl)-4-oxo-azetidin-2-yl]-acetylsulfanyl}-pyrrolidine-1-carboxylic acid 4-nitro-benzyl ester

Downstream raw materials:

(5R,6S)-6-[(R)-1-(4-Nitro-benzyloxycarbonyloxy)-ethyl]-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester

C₄₂H₄₈N₅O₁₈PS

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