(5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Base Information

• Chemical Name: (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid
• CAS No.: 852671-27-3
• Molecular Formula: C₂₇H₂₂N₂O₈S
• Molecular Weight: 534.546

Synonyms:(5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Chemical Property of (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

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Technology Process of (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid

There total 8 articles about (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid 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:

(5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (852671-30-8) → (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (852671-27-3)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; methoxybenzene; at 0 ℃; for 1h;

DOI:10.1021/ja036126o

Reference yield:

2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde (16851-02-8) → (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (852671-27-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: aq. NaOH / CH₂Cl₂ / 0.5 h / 20 °C

1.2: 28 percent / CH₂Cl₂ / 20 °C

2.1: m-CPBA / CH₂Cl₂ / 0.33 h

3.1: 16.71 mg / TFA / CH₂Cl₂; methoxybenzene / 1 h / 0 °C

With sodium hydroxide; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; methoxybenzene; 1.2: Wittig reaction;

DOI:10.1021/ja036126o

Reference yield:

7-hydroxy-2H-chromen-2-one (93-35-6) → (5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid (852671-27-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 82 percent / K₂CO₃ / dimethylformamide / 12 h / 115 °C

2.1: 63 percent / aq. HCl / CHCl₃ / 0.5 h / 0 °C

3.1: aq. NaOH / CH₂Cl₂ / 0.5 h / 20 °C

3.2: 28 percent / CH₂Cl₂ / 20 °C

4.1: m-CPBA / CH₂Cl₂ / 0.33 h

5.1: 16.71 mg / TFA / CH₂Cl₂; methoxybenzene / 1 h / 0 °C

With hydrogenchloride; sodium hydroxide; potassium carbonate; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; In dichloromethane; chloroform; methoxybenzene; N,N-dimethyl-formamide; 3.2: Wittig reaction;

DOI:10.1021/ja036126o

upstream raw materials:

(5S,6R,7R)-5,8-Dioxo-3-[(Z)-3-(2-oxo-2H-chromen-7-yloxy)-propenyl]-7-phenylacetylamino-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

7-hydroxy-2H-chromen-2-one

2-[(2-oxo-2H-chromen-7-yl)oxy]acetaldehyde

(6R,7R)-benzhydryl 3-(chloromethyl)-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

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