1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate

Base Information

• Chemical Name: 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate
• CAS No.: 75720-06-8
• Molecular Formula: C₂H₂O₄*C₁₉H₂₇N₃O₉
• Molecular Weight: 531.474
• Mol file: 75720-06-8.mol

Synonyms:1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate

Chemical Property of 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate

There total 3 articles about 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate 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: 92.0%

oxalic acid dihydrate (6153-56-6) + 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-β-D-glucopyranose (75719-88-9) → 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate (75720-06-8)

Guidance literature:

With hydrogen; palladium on activated charcoal; In 2-methoxy-ethanol; acetic acid; for 20h;

DOI:10.1016/S0008-6215(00)85517-2

Reference yield:

(5S)-5-benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid (37700-64-4) → 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate (75720-06-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 74 percent / dicyclohexylcarbodi-imide / dimethylformamide

2: imidazole / dimethylformamide / 24 h / Ambient temperature

3: 92 percent / H₂ / 10percent Pd/C / acetic acid; 2-methoxy-ethanol / 20 h

With 1H-imidazole; hydrogen; dicyclohexyl-carbodiimide; palladium on activated charcoal; In 2-methoxy-ethanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)85517-2

Reference yield:

N-benzyloxycarbonyl-L-phenylalanylglycylglycine pentachlorophenyl ester (75719-85-6) → 1-O-(L-phenylalanylglycylglycyl)-β-D-glucopyranose mono-oxalate (75720-06-8)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide / 24 h / Ambient temperature

2: 92 percent / H₂ / 10percent Pd/C / acetic acid; 2-methoxy-ethanol / 20 h

With 1H-imidazole; hydrogen; palladium on activated charcoal; In 2-methoxy-ethanol; acetic acid; N,N-dimethyl-formamide;

DOI:10.1016/S0008-6215(00)85517-2

upstream raw materials:

oxalic acid dihydrate

2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-β-D-glucopyranose

(5S)-5-benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid

N-benzyloxycarbonyl-L-phenylalanylglycylglycine pentachlorophenyl ester

Downstream raw materials:

β-D-glucose

L-phenylalanylglycylglycine

2,3,4,6-tetra-O-acetyl-1-O-(N-acetyl-L-phenylalanylglycylglycyl)-β-D-glucopyranose

Refernces