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

Base Information

• Chemical Name: 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-α-D-glucopyranose
• CAS No.: 75719-89-0
• Molecular Formula: C₅₅H₅₇N₃O₁₁
• Molecular Weight: 936.071

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

Chemical Property of 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-α-D-glucopyranose

Chemical Property:

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Technology Process of 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-α-D-glucopyranose

There total 2 articles about 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-α-D-glucopyranose 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)-5-benzyl-3,6,9-trioxo-1-phenyl-2-oxa-4,7,10-triazadodecan-12-oic acid (37700-64-4) → 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-α-D-glucopyranose (75719-89-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 74 percent / dicyclohexylcarbodi-imide / dimethylformamide

2: imidazole / dimethylformamide / 24 h / Ambient temperature

With 1H-imidazole; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

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

Reference yield:

2,3,4,6-tetra-O-benzyl-D-glucopyranose (6564-72-3) + N-benzyloxycarbonyl-L-phenylalanylglycylglycine pentachlorophenyl ester (75719-85-6) → 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-β-D-glucopyranose (75719-88-9) + 2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-α-D-glucopyranose (75719-89-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 24h; Yield given. Yields of byproduct given; Ambient temperature;

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

Reference yield: 88.0%

2,3,4,6-tetra-O-benzyl-1-O-(N-benzyloxycarbonyl-L-phenylalanylglycylglycyl)-α-D-glucopyranose (75719-89-0) + trifluoroacetic acid (76-05-1) → 1-O-(L-phenylalanylglycylglycyl)-α-D-glucopyranose trifluoroacetate (75720-09-1)

Guidance literature:

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

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

upstream raw materials:

2,3,4,6-tetra-O-benzyl-D-glucopyranose

N-benzyloxycarbonyl-L-phenylalanylglycylglycine pentachlorophenyl ester

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

Downstream raw materials:

1-O-(L-phenylalanylglycylglycyl)-α-D-glucopyranose trifluoroacetate

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