1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid

Base Information

• Chemical Name: 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid
• CAS No.: 1414867-53-0
• Molecular Formula: C₂₇H₃₃N₃O₉
• Molecular Weight: 543.574
• Mol file: 1414867-53-0.mol

Synonyms:

Chemical Property of 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid

There total 14 articles about 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic 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: 22.0%

prop-2-en-1-yl 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronate (1414867-52-9) → 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid (1414867-53-0)

Guidance literature:

With pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; at 25 ℃; for 1h; Inert atmosphere;

DOI:10.1021/jm301296t

Reference yield:

ethyl 3,5-dimethyl-6-oxo-1,6-dihydropyrazine-2-carboxylate (1166827-49-1) → 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid (1414867-53-0)

Guidance literature:

Multi-step reaction with 6 steps

1: trichlorophosphate / 0.17 h / 150 °C / Microwave irradiation

2: ammonia / methanol / 20 h / 20 °C

3: potassium dihydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,2-dimethoxyethane; ethanol / 0.5 h / 80 °C / Inert atmosphere

4: potassium hydroxide / tert-butyl alcohol / 2.5 h / 45 °C

5: HATU; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 17 h / 25 °C / Inert atmosphere

6: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere

With pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane; potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonia; HATU; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; water; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jm301296t

Reference yield:

ethyl 2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate (1166827-50-4) → 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronic acid (1414867-53-0)

Guidance literature:

Multi-step reaction with 7 steps

1: trifluoroacetic acid / 1,2-dichloro-ethane / 4 h / Reflux

2: trichlorophosphate / 0.17 h / 150 °C / Microwave irradiation

3: ammonia / methanol / 20 h / 20 °C

4: potassium dihydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / water; 1,2-dimethoxyethane; ethanol / 0.5 h / 80 °C / Inert atmosphere

5: potassium hydroxide / tert-butyl alcohol / 2.5 h / 45 °C

6: HATU; 1,4-diaza-bicyclo[2.2.2]octane / acetonitrile / 17 h / 25 °C / Inert atmosphere

7: pyrrolidine; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / tetrahydrofuran / 1 h / 25 °C / Inert atmosphere

With pyrrolidine; 1,4-diaza-bicyclo[2.2.2]octane; potassium dihydrogenphosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonia; HATU; trifluoroacetic acid; potassium hydroxide; trichlorophosphate; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; ethanol; water; 1,2-dichloro-ethane; acetonitrile; tert-butyl alcohol;

DOI:10.1021/jm301296t

upstream raw materials:

prop-2-en-1-yl 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronate

ethyl 2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate

ethyl 3,5-dimethyl-6-oxo-1,6-dihydropyrazine-2-carboxylate

ethyl 6-chloro-3,5-dimethylpyrazine-2-carboxylate