Hydroxy-{(2R,3S)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester

Base Information

• Chemical Name: Hydroxy-{(2R,3S)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester
• CAS No.: 78072-31-8
• Molecular Formula: C₃₄H₃₃N₅O₁₆S
• Molecular Weight: 799.726

Synonyms:

Chemical Property of Hydroxy-{(2R,3S)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of Hydroxy-{(2R,3S)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester

There total 5 articles about Hydroxy-{(2R,3S)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic 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:

2-(4-nitrobenzyloxycarbonylamino)ethanethiol (65750-59-6) → Hydroxy-{(2R,3S)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester (78072-31-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 900 mg / 4-dimethylaminopyridine, NN'-di-isopropylcarbodi-imide / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

2: 432 mg / activated 3A molecular sieves / dimethylformamide; toluene / 1.) room temperature, 12 h, 2.) 50 deg C, 4 h

With dmap; N,N'-di-isopropylcarbodiimide; 3 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide; toluene;

DOI:10.1039/P19810000964

Reference yield:

(3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine (72789-82-3,72843-58-4,73890-31-0,73890-76-3,77447-98-4,78342-09-3,78822-11-4,79057-48-0,79299-23-3,79952-71-9) → Hydroxy-{(2R,3S)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester (78072-31-8)

Guidance literature:

Multi-step reaction with 4 steps

1: 80percent aq. acetic acid / 4 h / 55 - 60 °C

2: 1.40 g / 8N Jones reagent / acetone / 0 °C

3: 900 mg / 4-dimethylaminopyridine, NN'-di-isopropylcarbodi-imide / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

4: 432 mg / activated 3A molecular sieves / dimethylformamide; toluene / 1.) room temperature, 12 h, 2.) 50 deg C, 4 h

With dmap; jones reagent; N,N'-di-isopropylcarbodiimide; acetic acid; 3 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1039/P19810000964

Reference yield:

(3S,4R)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-4-(2-oxoethyl)-2-oxoazetidine (64066-71-3,67314-42-5,71869-79-9,72778-03-1,77447-99-5,80559-32-6) → Hydroxy-{(2R,3S)-2-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanylcarbonylmethyl]-3-[(R)-1-(4-nitro-benzyloxycarbonyloxy)-ethyl]-4-oxo-azetidin-1-yl}-acetic acid 4-nitro-benzyl ester (78072-31-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.40 g / 8N Jones reagent / acetone / 0 °C

2: 900 mg / 4-dimethylaminopyridine, NN'-di-isopropylcarbodi-imide / CH₂Cl₂ / 1.) 0 deg C, 30 min, 2.) room temperature, 3 h

3: 432 mg / activated 3A molecular sieves / dimethylformamide; toluene / 1.) room temperature, 12 h, 2.) 50 deg C, 4 h

With dmap; jones reagent; N,N'-di-isopropylcarbodiimide; 3 A molecular sieve; In dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1039/P19810000964

upstream raw materials:

p-nitrobenzyl α-ethoxy-α-hydroxyacetate

(+/-)-4β-<<2-(p-nitrobenzyloxycarbonylamino)ethylthio>carbonylmethyl>-3α-<(1R^*)-1-(p-nitrobenzyloxycarbonyloxy)ethyl>azetidin-2-one

2-(4-nitrobenzyloxycarbonylamino)ethanethiol

(3S,4R)-4-(2,2-dimethoxyethyl)-3-[(1RS)-1-(p-nitrobenzyloxycarbonyloxy)ethyl]-2-oxoazetidine

Downstream raw materials:

(+/-)-4α-<<2-(p-nitrobenzyloxycarbonylamino)ethylthio>carbonylmethyl>-3β-<(1R^*)-1(p-nitrobenzyloxycarbonyloxy)ethyl>-1-azetidin-2-one

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