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

Base Information

• Chemical Name: (4R,6R,7R)-4-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
• CAS No.: 86766-52-1
• Molecular Formula: C₃₇H₂₈N₄O₄S₅
• Molecular Weight: 752.984

Synonyms:(4R,6R,7R)-4-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Chemical Property of (4R,6R,7R)-4-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of (4R,6R,7R)-4-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

There total 9 articles about (4R,6R,7R)-4-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic 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: 9.0%

2-[(2R,3R)-2-(Benzothiazol-2-yldisulfanyl)-4-oxo-3-phenylacetylamino-azetidin-1-yl]-4-(benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-but-2-enoic acid benzyl ester (86766-50-9) → (4R,6R,7R)-4-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (86766-52-1) + 2-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzyl ester (86784-85-2)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; at -78 ℃; for 0.5h;

DOI:10.1021/jo00168a036

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) → (4R,6R,7R)-4-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (86766-52-1)

Guidance literature:

Multi-step reaction with 6 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: 68 percent / acetone / 1 h / 0 - 5 °C

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

6: 64 percent / DBU / tetrahydrofuran / 0.5 h / -78 °C

With hydrogenchloride; sulfuric acid; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; sodium chloride; zinc; In tetrahydrofuran; dichloromethane; chloroform; water; acetone;

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) → (4R,6R,7R)-4-(Benzothiazol-2-ylsulfanyl)-3-(benzothiazol-2-ylsulfanylmethyl)-8-oxo-7-phenylacetylamino-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester (86766-52-1)

Guidance literature:

Multi-step reaction with 5 steps

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

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

3: 68 percent / acetone / 1 h / 0 - 5 °C

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

5: 64 percent / DBU / tetrahydrofuran / 0.5 h / -78 °C

With hydrogenchloride; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; zinc; In tetrahydrofuran; dichloromethane; acetone;

DOI:10.1021/jo00168a036

upstream raw materials:

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

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

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