(R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester

Base Information

• Chemical Name: (R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester
• CAS No.: 59203-76-8
• Molecular Formula: C₁₇H₁₈N₂O₄S
• Molecular Weight: 346.407
• Mol file: 59203-76-8.mol

Synonyms:(R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester

Chemical Property of (R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester

There total 9 articles about (R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl 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: 87.0%

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide (10209-03-7) → (R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester (59203-76-8)

Guidance literature:

With magnesium sulfate; phosphorous acid trimethyl ester; In benzene; Heating;

DOI:10.1139/v01-100

Reference yield:

penicillin V potassium (132-98-9) → (R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester (59203-76-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 94 percent / dimethylformamide / 17 h / 20 °C

2: 78 percent / hydrogen peroxide; glacial acetic acid / CH₂Cl₂ / 18 h

3: 87 percent / trimethyl phosphite; magnesium sulfate / benzene / Heating

With dihydrogen peroxide; magnesium sulfate; acetic acid; phosphorous acid trimethyl ester; In dichloromethane; N,N-dimethyl-formamide; benzene;

DOI:10.1139/v01-100

Reference yield:

methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate (2315-05-1) → (R)-3-methyl-2-((1R)-7-oxo-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-6-yl)-but-3-enoic acid methyl ester (59203-76-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / hydrogen peroxide; glacial acetic acid / CH₂Cl₂ / 18 h

2: 87 percent / trimethyl phosphite; magnesium sulfate / benzene / Heating

With dihydrogen peroxide; magnesium sulfate; acetic acid; phosphorous acid trimethyl ester; In dichloromethane; benzene;

DOI:10.1139/v01-100

upstream raw materials:

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide

methyl 2-(3-phenoxymethyl-4,5-dithia-2,7-diazabicyclo<4.2.0>oct-2-en-8-one-7-yl)-3-methylbut-3-enoate

penicillin V potassium

methyl (2S,5R,6R)-3,3-dimethyl-7-oxo-6-(2-phenoxyacetamido)-4-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate

Downstream raw materials:

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one

(6R,7R)-7-(phenoxyacetamido)ceph-3-em-4-carboxylic acid

3-Methyl-2-((1R,5R)-3-methyl-7-oxo-4-thia-2,6-diaza-bicyclo[3.2.0]hept-6-yl)-but-3-enoic acid methyl ester

3-Methyl-2-((1R,5R)-7-oxo-3-phenoxymethyl-4-thia-2,6-diaza-bicyclo[3.2.0]hept-6-yl)-but-3-enoic acid methyl ester