(6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 1026003-88-2
• Molecular Formula: C₆₂H₅₀ClN₇O₁₀S₂
• Molecular Weight: 1152.7

Synonyms:

Chemical Property of (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 10 articles about (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-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: 96.0%

7-amino-3-chloromethyl-3-cephem-4-carboxylic acid + {(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-[2-(trityl-amino)-thiazol-4-yl]-acetic acid (159048-31-4) → (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1026003-88-2)

Guidance literature:

With pyridine; trichlorophosphate;

DOI:10.7164/antibiotics.50.279

Reference yield:

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one (501-30-4,123712-78-7) → (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1026003-88-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 41 percent / K₂CO₃

2.1: 84 percent / triethylamine

3.2: NH₂OH*HCl

3.3: 48 percent / pyridine

4.1: NaBH₄

4.2: 64 percent / CBr₄; Ph₃P

5.1: N-hydroxyphtalimide

5.2: 79 percent / NH₂NH₂*H₂O

6.1: 95 percent

7.1: 96 percent / POCl₃; pyridine

With pyridine; sodium tetrahydroborate; N-hydroxyphthalimide; potassium carbonate; triethylamine; trichlorophosphate; 1.1: Substitution / 1.2: Substitution / 2.1: Addition / 3.1: Oxidation / 3.2: Condensation / 3.3: Cyclization / 4.1: Reduction / 4.2: Bromination / 5.1: Substitution / 5.2: Ring cleavage / 6.1: Condensation / 7.1: Substitution;

DOI:10.7164/antibiotics.50.279

Reference yield:

p-methoxybenzyl chloride (824-94-2) → (6R,7R)-7-{2-{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-3-chloromethyl-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (1026003-88-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 41 percent / K₂CO₃

2.1: 84 percent / triethylamine

3.2: NH₂OH*HCl

3.3: 48 percent / pyridine

4.1: NaBH₄

4.2: 64 percent / CBr₄; Ph₃P

5.1: N-hydroxyphtalimide

5.2: 79 percent / NH₂NH₂*H₂O

6.1: 95 percent

7.1: 96 percent / POCl₃; pyridine

With pyridine; sodium tetrahydroborate; N-hydroxyphthalimide; potassium carbonate; triethylamine; trichlorophosphate; 1.1: Substitution / 1.2: Substitution / 2.1: Addition / 3.1: Oxidation / 3.2: Condensation / 3.3: Cyclization / 4.1: Reduction / 4.2: Bromination / 5.1: Substitution / 5.2: Ring cleavage / 6.1: Condensation / 7.1: Substitution;

DOI:10.7164/antibiotics.50.279

upstream raw materials:

{(Z)-3-[4-Benzhydryloxy-5-(4-methoxy-benzyloxy)-1-oxy-pyridin-2-yl]-isoxazol-5-ylmethoxyimino}-[2-(trityl-amino)-thiazol-4-yl]-acetic acid

5-hydroxy-2-(hydroxymethyl)-4H-pyran-4-one

p-methoxybenzyl chloride

2-oxo-2-(2-(tritylamino)thiazol-4-yl)acetic acid

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