<6R,7R(Z)>-7-<<<2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid

Base Information

• Chemical Name: <6R,7R(Z)>-7-<<<2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid
• CAS No.: 122005-44-1
• Molecular Formula: C₂₂H₂₀N₆O₁₀S₂
• Molecular Weight: 592.567
• Mol file: 122005-44-1.mol

Synonyms:

Chemical Property of <6R,7R(Z)>-7-<<<2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of <6R,7R(Z)>-7-<<<2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid

There total 4 articles about <6R,7R(Z)>-7-<<<2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid 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:

3,4-Diacetoxy-benzoesaeure (58534-64-8) → <6R,7R(Z)>-7-<<<2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid (122005-44-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine, N-methyl-2-fluoropyridinium tosylate / 1.) CH₂Cl₂, 0 deg C, 1h, 2. a) 0 deg C, 20 min, b) up to r.t.

2: 76 percent / anisole, trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.) NaHCO₃, 2.) NaHCO₃ / 1.) THF, H₂O, r.t., 5 h, 2.) MeOH, r.t., 2 h

With sodium hydrogencarbonate; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methoxybenzene; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00040a057

Reference yield:

N-(tert-butyloxycarbonyl)-3-deacetylcephalosporanic acid (37051-06-2) → <6R,7R(Z)>-7-<<<2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid (122005-44-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine, N-methyl-2-fluoropyridinium tosylate / 1.) CH₂Cl₂, 0 deg C, 1h, 2. a) 0 deg C, 20 min, b) up to r.t.

2: 76 percent / anisole, trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

3: 1.) NaHCO₃, 2.) NaHCO₃ / 1.) THF, H₂O, r.t., 5 h, 2.) MeOH, r.t., 2 h

With sodium hydrogencarbonate; 1-methyl-2-fluoropyridinium p-toluenesulfonate; methoxybenzene; triethylamine; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00040a057

Reference yield:

(6R,7R)-3-<<<3,4-bis(acetyloxy)benzoyl>oxy>methyl>-7-<<(1,1-dimethylethoxy)carbonyl>amino>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid (139290-97-4) → <6R,7R(Z)>-7-<<<2-amino-2-oxoethoxy)imino>(2-amino-4-thiazolyl)acetyl>amino>-3-<<(3,4-dihydroxybenzoyl)oxy>methyl>-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-en-2-carboxylic acid (122005-44-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / anisole, trifluoroacetic acid / CH₂Cl₂ / 3 h / Ambient temperature

2: 1.) NaHCO₃, 2.) NaHCO₃ / 1.) THF, H₂O, r.t., 5 h, 2.) MeOH, r.t., 2 h

With sodium hydrogencarbonate; methoxybenzene; trifluoroacetic acid; In dichloromethane;

DOI:10.1021/jo00040a057

upstream raw materials:

(Z)-2-<<<1-(2-amino-4-thiazolyl)-2-<(2-benzothiazolyl)thio>-2-oxoethylidene>amino>oxy>ethanamide

(6R,7R)-<<<3,4-bis(acetyloxy)benzoyl>oxy>methyl>-7-amino-8-oxo-5-thia-1-azabicyclo<4.2.0>oct-2-ene-2-carboxylic acid trifluoroacetic acid salt

3,4-Diacetoxy-benzoesaeure

N-(tert-butyloxycarbonyl)-3-deacetylcephalosporanic acid