(6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester
• CAS No.: 155835-22-6
• Molecular Formula: C₄₁H₄₃N₅O₆S₂
• Molecular Weight: 765.954
• Mol file: 155835-22-6.mol

Synonyms:

Chemical Property of (6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

There total 9 articles about (6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl 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:

tetrahydropyran-2-carboxylic acid (51673-83-7) → (6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (155835-22-6)

Guidance literature:

Multi-step reaction with 9 steps

1: (COCl)2 / dimethylformamide; CH₂Cl₂

2: 2.) HCl

3: K₂CO₃ / dimethylformamide

4: NEt₃ / 1,2-dichloro-ethane

5: SOCl₂, 2,6-lutidine / tetrahydrofuran

6: dioxane

7: PhCOOH / toluene / Heating

8: 1.) PCl₅, N-methylmorpholine, 2.) CH₃OH / 1.) CH₂Cl₂

9: 1.) CH₃SO₂Cl, i-Pr₂NEt, 2.) pyridine / 1.) DMF

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; hydrogenchloride; methanol; thionyl chloride; oxalyl dichloride; phosphorus pentachloride; potassium carbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; benzoic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.7164/antibiotics.47.253

Reference yield:

tetrahydropyran-2-carboxylic acid chloride (147164-53-2,40053-81-4,154001-94-2) → (6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (155835-22-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 2.) HCl

2: K₂CO₃ / dimethylformamide

3: NEt₃ / 1,2-dichloro-ethane

4: SOCl₂, 2,6-lutidine / tetrahydrofuran

5: dioxane

6: PhCOOH / toluene / Heating

7: 1.) PCl₅, N-methylmorpholine, 2.) CH₃OH / 1.) CH₂Cl₂

8: 1.) CH₃SO₂Cl, i-Pr₂NEt, 2.) pyridine / 1.) DMF

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; hydrogenchloride; methanol; thionyl chloride; phosphorus pentachloride; potassium carbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; benzoic acid; In tetrahydrofuran; 1,4-dioxane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.7164/antibiotics.47.253

Reference yield:

2-(2-chloroacetyl)tetrahydropyran (141061-07-6) → (6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester (155835-22-6)

Guidance literature:

Multi-step reaction with 7 steps

1: K₂CO₃ / dimethylformamide

2: NEt₃ / 1,2-dichloro-ethane

3: SOCl₂, 2,6-lutidine / tetrahydrofuran

4: dioxane

5: PhCOOH / toluene / Heating

6: 1.) PCl₅, N-methylmorpholine, 2.) CH₃OH / 1.) CH₂Cl₂

7: 1.) CH₃SO₂Cl, i-Pr₂NEt, 2.) pyridine / 1.) DMF

With 4-methyl-morpholine; pyridine; 2,6-dimethylpyridine; methanol; thionyl chloride; phosphorus pentachloride; potassium carbonate; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; benzoic acid; In tetrahydrofuran; 1,4-dioxane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;

DOI:10.7164/antibiotics.47.253

upstream raw materials:

(6R,7R)-7-Amino-8-oxo-3-(S)-tetrahydro-pyran-2-yl-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid tert-butyl ester

2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid

tetrahydropyran-2-carboxylic acid

tetrahydropyran-2-carboxylic acid chloride