benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid

Base Information

• Chemical Name: benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid
• CAS No.: 174743-65-8
• Molecular Formula: C₆₀H₆₈N₄O₁₅
• Molecular Weight: 1085.22

Synonyms:benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid

Chemical Property of benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid

Chemical Property:

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Technology Process of benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid

There total 11 articles about benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic 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: 97.0%

benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid t-butyl ester (174743-64-7) → benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid (174743-65-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 7.5h; Ambient temperature;

DOI:10.1016/0040-4020(95)00963-9

Reference yield:

Cbz-D-Phe (2448-45-5) → benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid (174743-65-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 84 percent / dimethylaminopyridine, DCC / CH₂Cl₂ / 20 h

2: 100 percent / TFA / CH₂Cl₂ / 5 h / Ambient temperature

3: 86 percent / dimethylaminopyridine, DCC / CH₂Cl₂ / 84 h / 0 °C

4: 99 percent / H₂, AcOH / 10percent Pd/C / ethyl acetate / 9 h / Ambient temperature

5: 55 percent / dimethylaminopyridine, DCC / CH₂Cl₂ / 72 h / 0 °C

6: 97 percent / TFA / CH₂Cl₂ / 7.5 h / Ambient temperature

With dmap; hydrogen; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1016/0040-4020(95)00963-9

Reference yield:

N-Cbz-L-Phe (1161-13-3) → benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid (174743-65-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 99 percent / dimethylaminopyridine, DCC / CH₂Cl₂ / 14 h

2: 99 percent / H₂ / 10percent Pd/C / ethyl acetate / 5 h / Ambient temperature

3: 86 percent / dimethylaminopyridine, DCC / CH₂Cl₂ / 84 h / 0 °C

4: 99 percent / H₂, AcOH / 10percent Pd/C / ethyl acetate / 9 h / Ambient temperature

5: 55 percent / dimethylaminopyridine, DCC / CH₂Cl₂ / 72 h / 0 °C

6: 97 percent / TFA / CH₂Cl₂ / 7.5 h / Ambient temperature

With dmap; hydrogen; acetic acid; dicyclohexyl-carbodiimide; trifluoroacetic acid; palladium on activated charcoal; In dichloromethane; ethyl acetate;

DOI:10.1016/0040-4020(95)00963-9

upstream raw materials:

benzyloxycarbonyl D-phenylalanyl L-α-hydroxyisovaleryl L-phenylalanyl D-lactyl D-phenylalanyl L-α-hydroisovaleryl L-phenylalanyl D-lactic acid t-butyl ester

N-Cbz-L-Phe

Cbz-D-Phe

L-α-hydroxyisovaleric acid t-butyl ester

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