(6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester

Base Information

• Chemical Name: (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester
• CAS No.: 380413-10-5
• Molecular Formula: C₃₁H₂₈N₂O₈S
• Molecular Weight: 588.638

Synonyms:(6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester

Chemical Property of (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester

There total 13 articles about (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl 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: 52.0%

(4R,5S,6R,7R)-4-Iodomethyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester → (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester (380413-10-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.666667h;

DOI:10.1139/v01-100

Reference yield:

(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one (35500-75-5) → (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester (380413-10-5)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 49 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 0 °C

2.1: sodium hydride / dimethylformamide / 0 - 20 °C

2.2: 34 percent / dimethylformamide / 16.6 h / 0 - 20 °C

3.1: 74 percent / iodine / CH₂Cl₂; H₂O / 3.5 h

4.1: 62 percent / sodium periodate / methanol; H₂O / 2 h / 60 °C

5.1: 52 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.67 h

With sodium periodate; iodine; N-benzyl-trimethylammonium hydroxide; sodium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1139/v01-100

Reference yield:

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-2-enoic acid methyl ester (380412-94-2) → (6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester (380413-10-5)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 78 percent / potassium permanganate; magnesium sulfate / H₂O; ethanol

2.1: 49 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 0 °C

3.1: sodium hydride / dimethylformamide / 0 - 20 °C

3.2: 34 percent / dimethylformamide / 16.6 h / 0 - 20 °C

4.1: 74 percent / iodine / CH₂Cl₂; H₂O / 3.5 h

5.1: 62 percent / sodium periodate / methanol; H₂O / 2 h / 60 °C

6.1: 52 percent / 1,8-diazobicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 0.67 h

With potassium permanganate; sodium periodate; iodine; N-benzyl-trimethylammonium hydroxide; sodium hydride; magnesium sulfate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1139/v01-100

upstream raw materials:

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

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-2-enoic acid methyl ester

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide

malonic acid dibenzyl ester

Downstream raw materials:

(6R,7R)-4-Methylene-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid dibenzyl ester

(6R,7R)-4-Methyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2,2-dicarboxylic acid dibenzyl ester

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