4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid benzyl ester

Base Information

• Chemical Name: 4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid benzyl ester
• CAS No.: 86766-51-0
• Molecular Formula: C₄₂H₃₅N₃O₈S₅
• Molecular Weight: 870.085

Synonyms:4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid benzyl ester

Chemical Property of 4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of 4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid benzyl ester

There total 7 articles about 4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid 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:

(R)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3-methyl-but-3-enoic acid benzyl ester (86832-59-9) → 4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid benzyl ester (86766-51-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 50 percent / NaCl, conc. H₂SO₄ / CHCl₃; H₂O / Ambient temperature; 1) electrolysis, Pt electrodes, undivided cell, 10 mA/cm², 15 F/mol, 2) electrolysis 5 F/mol, irradiation

2: 96 percent / Zn powder, AcOH / CH₂Cl₂ / 0.5 h / 0 °C

3: 86 percent / Et₃N / CH₂Cl₂ / 2 h / 5 - 15 °C

4: 60 percent / dimethylformamide / 1.5 h / 80 °C

5: 1) 5percent HCl / 1) dioxane, room temp., 30 min, 2) room temp., 30 min

With hydrogenchloride; sulfuric acid; acetic acid; triethylamine; sodium chloride; zinc; In dichloromethane; chloroform; water; N,N-dimethyl-formamide;

DOI:10.1021/jo00168a036

Reference yield:

Benzyl 3-(Choromethyl)-3,4-dichloro-2-<3-(phenyldichloromethyl)-7-oxo-4-thia-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl>butanoate (86832-61-3) → 4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid benzyl ester (86766-51-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 96 percent / Zn powder, AcOH / CH₂Cl₂ / 0.5 h / 0 °C

2: 86 percent / Et₃N / CH₂Cl₂ / 2 h / 5 - 15 °C

3: 60 percent / dimethylformamide / 1.5 h / 80 °C

4: 1) 5percent HCl / 1) dioxane, room temp., 30 min, 2) room temp., 30 min

With hydrogenchloride; acetic acid; triethylamine; zinc; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00168a036

Reference yield:

(R)-3-Chloromethyl-2-[(1R,5R)-3-(dichloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-but-3-enoic acid benzyl ester (86832-60-2) → 4-Benzenesulfonyl-3-benzenesulfonylmethyl-2-[(2R,3R)-2-(benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-but-2-enoic acid benzyl ester (86766-51-0)

Guidance literature:

Multi-step reaction with 5 steps

1: 98 percent / Cl₂ / CH₂Cl₂; CCl₄ / 0.17 h / Ambient temperature; Irradiation

2: 96 percent / Zn powder, AcOH / CH₂Cl₂ / 0.5 h / 0 °C

3: 86 percent / Et₃N / CH₂Cl₂ / 2 h / 5 - 15 °C

4: 60 percent / dimethylformamide / 1.5 h / 80 °C

5: 1) 5percent HCl / 1) dioxane, room temp., 30 min, 2) room temp., 30 min

With hydrogenchloride; chlorine; acetic acid; triethylamine; zinc; In tetrachloromethane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00168a036

upstream raw materials:

sodium benzenesulfonate

Benzyl 2-(3-Benzyl-7-oxo-4-thia-2,6-diazabicyclo<3.2.0>hept-2-en-6-yl)-4-chloro-3-(chloromethyl)-2-butenoate

(S)-2-((1R,5R)-3-Benzyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-3,4-dichloro-3-chloromethyl-butyric acid benzyl ester

4-Chloro-3-chloromethyl-2-[(1R,5R)-3-(dichloro-phenyl-methyl)-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl]-but-2-enoic acid benzyl ester

Downstream raw materials:

(4R,6R,7R)-4-Benzenesulfonyl-3-benzenesulfonylmethyl-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

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