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

Base Information

• Chemical Name: (4R,6R,7R)-4-Iodomethyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester
• CAS No.: 380413-09-2
• Molecular Formula: C₂₅H₂₅IN₂O₈S
• Molecular Weight: 640.453
• Mol file: 380413-09-2.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (4R,6R,7R)-4-Iodomethyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester 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: 52.0%

(4R,6R,7R)-4-Iodomethyl-8-oxo-7-(2-phenoxy-acetylamino)-5-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester (380413-07-0) → (4R,6R,7R)-4-Iodomethyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester (380413-09-2)

Guidance literature:

With sodium periodate; In methanol; water; at 35 ℃; for 2.5h;

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) → (4R,6R,7R)-4-Iodomethyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester (380413-09-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 75 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

2: 83 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / 2 h / 0 °C

3: 94 percent / iodine / CH₂Cl₂; H₂O / 5.5 h / 20 °C

4: 52 percent / sodium periodate / methanol; H₂O / 2.5 h / 35 °C

With sodium periodate; iodine; N-benzyl-trimethylammonium hydroxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1139/v01-100

Reference yield:

methyl 6β-phenoxyacetamidopenicillanate-1β-sulfoxide (10209-03-7) → (4R,6R,7R)-4-Iodomethyl-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ4-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester (380413-09-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / trimethyl phosphite; magnesium sulfate / benzene / Heating

2: 62 percent / triethylamine / CH₂Cl₂ / 3 h

3: 78 percent / potassium permanganate; magnesium sulfate / H₂O; ethanol

4: 75 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

5: 83 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / 2 h / 0 °C

6: 94 percent / iodine / CH₂Cl₂; H₂O / 5.5 h / 20 °C

7: 52 percent / sodium periodate / methanol; H₂O / 2.5 h / 35 °C

With potassium permanganate; sodium periodate; iodine; N-benzyl-trimethylammonium hydroxide; magnesium sulfate; triethylamine; phosphorous acid trimethyl ester; In methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1139/v01-100

upstream raw materials:

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

(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

Downstream raw materials:

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

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

(2R,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 benzyl ester methyl ester

(2S,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 benzyl ester methyl ester