4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate

Base Information

• Chemical Name: 4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate
• CAS No.: 127108-57-0
• Molecular Formula: C₄₁H₃₆IN₅O₆S₂
• Molecular Weight: 885.803
• Mol file: 127108-57-0.mol

Synonyms:4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property of 4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate

There total 3 articles about 4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate 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:

4-methoxybenzyl-(Z)-3-(chloromethyl)-7-(2-(methoxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate (116252-38-1) → 4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate (127108-57-0)

Guidance literature:

With sodium iodide; In acetone;

DOI:10.7164/antibiotics.47.1526

Reference yield:

2-(2-aminothiazol-4-yl)-2-(methoxy)iminoacetic acid (64485-90-1) → 4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate (127108-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 87 percent / pyridine, POCl₃ / CH₂Cl₂ / 0.33 h / -20 °C

2: NaI / acetone / 1 h / Ambient temperature

With pyridine; sodium iodide; trichlorophosphate; In dichloromethane; acetone;

DOI:10.1016/S0968-0896(98)00103-5

Reference yield:

para-methoxybenzyl (6R,7R)-7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride → 4-methoxybenzyl (6R,7R)7β-{2-{2-aminotrityl-1,3-thiazol-4-yl}-2-[(Z)-methoxyimino]-acetylamino}-3-(iodomethyl)-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylate (127108-57-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) 1-hydroxybenzotriazole, DCC, 2.) Et₃N / 1.) DMF, 2.) DMF

2: NaI / acetone

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; sodium iodide; In acetone;

DOI:10.7164/antibiotics.47.1526

upstream raw materials:

4-methoxybenzyl-(Z)-3-(chloromethyl)-7-(2-(methoxyimino)-2-(2-(tritylamino)thiazol-4-yl)acetamido)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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

Downstream raw materials:

(6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(thiazolo[5,4-c]pyridin-2-ylsulfanylmethyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

(6R,7R)-7-{2-[(Z)-Methoxyimino]-2-[2-(trityl-amino)-thiazol-4-yl]-acetylamino}-8-oxo-3-(thiazolo[4,5-b]pyridin-2-ylsulfanylmethyl)-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 4-methoxy-benzyl ester

N-[[{2-(4-methoxybenzylcarbonyl)}-(6R,7R)-7β-{2-(2-aminotrityl-1,3-thiazol-4-yl)-2-[(Z)-methoxyimino]-acetylamino}-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-3yl]methyl]-N,N-dimethyl-N-[(R)-1-(4-chlorophenyl)]ethanaminium iodide

4-methoxyphenylmethyl 7-<(Z)-2-(2-tritylaminothiazol-4-yl)-2-methoxyiminoacetamido>-3-<(Z)-3-tert-butyldimethylsilyloxy-1-propenyl>-3-cephem-4-carboxylate