(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

Base Information

Chemical Name:(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
CAS No.:380413-15-0
Molecular Formula:C₂₅H₂₄N₂O₇S
Molecular Weight:496.541
Hs Code.:

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 13 articles about (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 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: 79.0%

: 380413-12-7
(2S,6R,7R)-4-Methylene-5,8-dioxo-7-(2-phenoxy-acetylamino)-5λ⁴-thia-1-aza-bicyclo[4.2.0]octane-2,2-dicarboxylic acid benzyl ester methyl ester

: 380413-15-0
(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

Guidance literature:: With phosphorus tribromide; In N,N-dimethyl-formamide; at 0 ℃; for 0.333333h;
DOI:10.1139/v01-100

Reference yield:

: 35500-75-5
(1R)-3-phenoxymethyl-(1rH,5cH)-4-thia-2,6-diaza-bicyclo[3.2.0]hept-2-en-7-one

: 380413-15-0
(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

Guidance literature:: Multi-step reaction with 6 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

5: 207 mg / 1,8-diazobicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1.5 h

6: 79 percent / phosphorus tribromide / dimethylformamide / 0.33 h / 0 °C

With sodium periodate; iodine; phosphorus tribromide; N-benzyl-trimethylammonium hydroxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1139/v01-100

Reference yield:

: 380412-94-2
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

: 380413-15-0
(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

Guidance literature:: Multi-step reaction with 7 steps

1: 78 percent / potassium permanganate; magnesium sulfate / H₂O; ethanol

2: 75 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / -55 - 20 °C

3: 83 percent / benzyltrimethylammonium hydroxide / dimethylformamide; methanol / 2 h / 0 °C

4: 94 percent / iodine / CH₂Cl₂; H₂O / 5.5 h / 20 °C

5: 52 percent / sodium periodate / methanol; H₂O / 2.5 h / 35 °C

6: 207 mg / 1,8-diazobicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1.5 h

7: 79 percent / phosphorus tribromide / dimethylformamide / 0.33 h / 0 °C

With potassium permanganate; sodium periodate; iodine; phosphorus tribromide; N-benzyl-trimethylammonium hydroxide; 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