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

Base Information

• Chemical Name: prop-2-en-1-yl 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronate
• CAS No.: 1414867-52-9
• Molecular Formula: C₃₀H₃₇N₃O₉
• Molecular Weight: 583.638
• Mol file: 1414867-52-9.mol

Synonyms:

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 13 articles about prop-2-en-1-yl 1-O-({trans-4-[4-(6-carbamoyl-3,5-dimethylpyrazin-2-yl)phenyl]cyclohexyl}acetyl)-β-D-glucopyranuronate 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:

ethyl 3,5-dimethyl-6-oxo-1,6-dihydropyrazine-2-carboxylate (1166827-49-1) → 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)

Guidance literature:

Multi-step reaction with 5 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

With 1,4-diaza-bicyclo[2.2.2]octane; potassium dihydrogenphosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; ammonia; HATU; potassium hydroxide; trichlorophosphate; In 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) → 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)

Guidance literature:

Multi-step reaction with 6 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

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

DOI:10.1021/jm301296t

Reference yield:

ethyl 6-chloro-3,5-dimethylpyrazine-2-carboxylate (1166827-48-0) → 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)

Guidance literature:

Multi-step reaction with 4 steps

1: ammonia / methanol / 20 h / 20 °C

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

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

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

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

DOI:10.1021/jm301296t

upstream raw materials:

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

tert-butyl [4-(4-hydroxyphenyl)cyclohexylidene]acetate

Downstream raw materials:

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