methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate

Base Information

• Chemical Name: methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate
• CAS No.: 1312312-95-0
• Molecular Formula: C₂₆H₂₈N₂O₁₂
• Molecular Weight: 560.515
• Mol file: 1312312-95-0.mol

Synonyms:methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate

Chemical Property of methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate

There total 5 articles about methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate 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: 78.0%

5-bromopyrimidine-2-carboxylic acid methyl ester (89581-38-4) + 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl 2,3,4,6-tetra-O-acetyl-α-D-mannopyranoside (1295649-89-6) → methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate (1312312-95-0)

Guidance literature:

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 80 ℃; Inert atmosphere;

Reference yield:

per-O-acetyl-α-D-mannopyranose (4163-65-9) → methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate (1312312-95-0)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrazinium monoacetate / N,N-dimethyl-formamide / 3 h / 20 °C / Inert atmosphere

2: caesium carbonate / dichloromethane / 3.5 h / 20 °C / Inert atmosphere

3: trimethylsilyl trifluoromethanesulfonate / toluene / 2.5 h / 20 °C / Inert atmosphere

4: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 2 h / 120 °C / Microwave irradiation; Inert atmosphere

5: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With potassium phosphate; trimethylsilyl trifluoromethanesulfonate; potassium acetate; hydrazinium monoacetate; caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dichloromethane; N,N-dimethyl-formamide; toluene;

Reference yield:

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose (22860-22-6) → methyl 5-[4-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyloxy)phenyl]-pyrimidine-2-carboxylate (1312312-95-0)

Guidance literature:

Multi-step reaction with 4 steps

1: caesium carbonate / dichloromethane / 3.5 h / 20 °C / Inert atmosphere

2: trimethylsilyl trifluoromethanesulfonate / toluene / 2.5 h / 20 °C / Inert atmosphere

3: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 2 h / 120 °C / Microwave irradiation; Inert atmosphere

4: potassium phosphate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / N,N-dimethyl-formamide / 80 °C / Inert atmosphere

With potassium phosphate; trimethylsilyl trifluoromethanesulfonate; potassium acetate; caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In dichloromethane; N,N-dimethyl-formamide; toluene;

upstream raw materials:

per-O-acetyl-α-D-mannopyranose

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate

2,3,4,6-tetra-O-acetyl-α-D-mannopyranose

5-bromopyrimidine-2-carboxylic acid methyl ester