(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(N-methylamidomethyl)phenylcarbonylmethyl>-azetidin-2-one

Base Information

• Chemical Name: (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(N-methylamidomethyl)phenylcarbonylmethyl>-azetidin-2-one
• CAS No.: 88140-23-2
• Molecular Formula: C₅₁H₄₅N₄O₁₂P
• Molecular Weight: 936.912

Synonyms:

Chemical Property of (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(N-methylamidomethyl)phenylcarbonylmethyl>-azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(N-methylamidomethyl)phenylcarbonylmethyl>-azetidin-2-one

There total 8 articles about (3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(N-methylamidomethyl)phenylcarbonylmethyl>-azetidin-2-one 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:

4-bromophenethanol (4654-39-1) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(N-methylamidomethyl)phenylcarbonylmethyl>-azetidin-2-one (88140-23-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 78 percent / Et₃N / CH₂Cl₂ / 0 °C

3: 65 percent / conc HCl / dimethylformamide / 0.2 h / Ambient temperature

4: Jones reagent / acetone / 1 h / Ambient temperature

5: 1) carbonyldiimidazole, 2) Et₃N / 1) CH₂Cl₂, 2 h, RT, 2) CH₂Cl₂, 4 h, RT

With hydrogenchloride; jones reagent; triethylamine; 1,1'-carbonyldiimidazole; In dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

1-(t-butyldimethylsilyloxy)-2-(4-bromophenyl)ethane (73899-15-7) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(N-methylamidomethyl)phenylcarbonylmethyl>-azetidin-2-one (88140-23-2)

Guidance literature:

Multi-step reaction with 4 steps

2: 65 percent / conc HCl / dimethylformamide / 0.2 h / Ambient temperature

3: Jones reagent / acetone / 1 h / Ambient temperature

4: 1) carbonyldiimidazole, 2) Et₃N / 1) CH₂Cl₂, 2 h, RT, 2) CH₂Cl₂, 4 h, RT

With hydrogenchloride; jones reagent; triethylamine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)92147-7

Reference yield:

{(2R,3S)-2-(2-Hydroxy-ethyl)-3-[(R)-1-(2-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-(triphenyl-λ5-phosphanylidene)-acetic acid 2-nitro-benzyl ester (88198-12-3) → (3S*,4R*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-<4'-(N-methylamidomethyl)phenylcarbonylmethyl>-azetidin-2-one (88140-23-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 96 percent / Jones reagent / acetone

2: 54 percent / Et₃N / 0.67 h / 0 °C

4: 65 percent / conc HCl / dimethylformamide / 0.2 h / Ambient temperature

5: Jones reagent / acetone / 1 h / Ambient temperature

6: 1) carbonyldiimidazole, 2) Et₃N / 1) CH₂Cl₂, 2 h, RT, 2) CH₂Cl₂, 4 h, RT

With hydrogenchloride; jones reagent; triethylamine; 1,1'-carbonyldiimidazole; In N,N-dimethyl-formamide; acetone;

DOI:10.1016/S0040-4020(01)92147-7

upstream raw materials:

(3S^*,4R^*)-1-(o-nitrobenzyloxycarbonyltriphenylphosphoranylidene)methyl-3-<(R^*)-1-(o-nitrobenzyloxycarbonyloxy)ethyl>-4-(4'-carboxymethylphenyl)carbonylmethyl-azetidin-2-one

methylamine

4-bromophenethanol

1-(t-butyldimethylsilyloxy)-2-(4-bromophenyl)ethane

Downstream raw materials:

(5R^*,6S^*)-2-<4'-(N-methylamidomethyl)phenyl>-6-<(R^*)-1-hydroxyethyl>-1-carbapen-2-em-3-carboxylic acid

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