benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide

Base Information

• Chemical Name: benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide
• CAS No.: 81092-96-8
• Molecular Formula: C₄₃H₅₃N₇O₉S
• Molecular Weight: 844.001
• Mol file: 81092-96-8.mol

Synonyms:benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide

Chemical Property of benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide

There total 8 articles about benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide 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:

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester (47307-26-6,149967-07-7) → benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide (81092-96-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 71 percent / dicyclohexylcarbodiimide / ethyl acetate / 1.) 0 deg C, 0.5 h, 2.) RT, 12 h

2: 91 percent / diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide / Ambient temperature

3: H₂ / 10percent Pd/C / ethanol; dimethylformamide

4: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) RT

5: H₂, diisopropylethylamine (DIEA) / 10percent Pd/BaSO₄ / dimethylformamide; H₂O / 12 h

6: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) RT, overnight

7: H₂, diisopropylethylamine (DIEA) / 10percent Pd/BaSO₄ / dimethylformamide; H₂O

8: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide

With hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; Pd-BaSO₄; In ethanol; water; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm00347a019

Reference yield:

benzyloxycarbonyl-L-aspartic acid α-tert-butyl β-p-nitrophenyl ester (6997-15-5) → benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide (81092-96-8)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide / Ambient temperature

2: H₂ / 10percent Pd/C / ethanol; dimethylformamide

3: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) RT

4: H₂, diisopropylethylamine (DIEA) / 10percent Pd/BaSO₄ / dimethylformamide; H₂O / 12 h

5: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) RT, overnight

6: H₂, diisopropylethylamine (DIEA) / 10percent Pd/BaSO₄ / dimethylformamide; H₂O

7: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide

With hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; Pd-BaSO₄; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00347a019

Reference yield:

benzyloxycarbonyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide (81092-90-2) → benzyloxycarbonylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide (81092-96-8)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / 10percent Pd/C / ethanol; dimethylformamide

2: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) RT

3: H₂, diisopropylethylamine (DIEA) / 10percent Pd/BaSO₄ / dimethylformamide; H₂O / 12 h

4: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide / 1.) 0 deg C, 0.5 h, 2.) RT, overnight

5: H₂, diisopropylethylamine (DIEA) / 10percent Pd/BaSO₄ / dimethylformamide; H₂O

6: diisopropylethylamine (DIEA), hydroxybenzotriazole (HOBt) / dimethylformamide

With hydrogen; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; palladium on activated charcoal; Pd-BaSO₄; In ethanol; water; N,N-dimethyl-formamide;

DOI:10.1021/jm00347a019

upstream raw materials:

Z-Gly-ONp

(S)-2-{(S)-2-[(S)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-4-methylsulfanyl-butyrylamino}-N-((S)-1-carbamoyl-2-phenyl-ethyl)-succinamic acid tert-butyl ester

(S)-2-benzyloxycarbonylamino-succinic acid 1-tert-butyl ester

benzyloxycarbonyl-L-aspartic acid α-tert-butyl β-p-nitrophenyl ester

Downstream raw materials:

L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-β-L-phenylalanine amide

tert-butyloxycarbonyl-L-methionylglycyl-L-tryptophyl-L-methionyl-α-tert-butyl-L-aspartyl-β-L-phenylalanine amide

benzyloxycarbonyl-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-β-L-phenylalanine amide

benzyloxycarbonyl(O-sulfate)-L-tyrosyl-L-methionylglycyl-L-tryptophyl-L-methionyl-L-aspartyl-β-L-phenylalanine amide