N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe₂)-D-tryptophyl-L-leucine methyl ester

Base Information

• Chemical Name: N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe₂)-D-tryptophyl-L-leucine methyl ester
• CAS No.: 128718-87-6
• Molecular Formula: C₄₄H₅₈N₆O₇
• Molecular Weight: 782.981

Synonyms:N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe₂)-D-tryptophyl-L-leucine methyl ester

Chemical Property of N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe₂)-D-tryptophyl-L-leucine methyl ester

Chemical Property:

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Technology Process of N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe₂)-D-tryptophyl-L-leucine methyl ester

There total 10 articles about N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe₂)-D-tryptophyl-L-leucine methyl ester 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:

Cbz-D-Phe (2448-45-5) → N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe2)-D-tryptophyl-L-leucine methyl ester (128718-87-6)

Guidance literature:

Multi-step reaction with 4 steps

1: Et₃N, 1-hydroxybenzotriazole (HOBt), dicyclohexylcarbodiimide (DCCI) / dimethylformamide / 4 °C

2: 64.5 percent / 3N HCl / acetic acid / 0.5 h / Ambient temperature

3: Et₃N, molecular sieve / 1.5 h

4: sodium cyanoborohydride, AcOH / acetone / 1.5 h

With hydrogenchloride; molecular sieve; sodium cyanoborohydride; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In acetic acid; N,N-dimethyl-formamide; acetone;

Reference yield:

methyl (L)-leucinate hydrochloride (7517-19-3) → N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe2)-D-tryptophyl-L-leucine methyl ester (128718-87-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 85.9 percent / dicyclohexylcarbodiimide (DCCI), 1-hydroxybenzotriazole (HOBt), Et₃N / dimethylformamide / 4 °C

2: 83.6 percent / 6N HCl, dithioethane / ethyl acetate / 1 h

3: 92 percent / Et₃N / dimethylformamide / Ambient temperature

4: H₂ / 5percent Pd/C / dimethylformamide; ethanol / 5 h

5: Et₃N, 1-hydroxybenzotriazole (HOBt), dicyclohexylcarbodiimide (DCCI) / dimethylformamide / 4 °C

6: 64.5 percent / 3N HCl / acetic acid / 0.5 h / Ambient temperature

7: Et₃N, molecular sieve / 1.5 h

8: sodium cyanoborohydride, AcOH / acetone / 1.5 h

With hydrogenchloride; molecular sieve; hydrogen; sodium cyanoborohydride; benzotriazol-1-ol; ethane-1,2-dithiol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;

Reference yield:

N-tert-butoxycarbonyl-D-tryptophyl-L-leucine methyl ester (128719-24-4) → N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(CHMe2)-D-tryptophyl-L-leucine methyl ester (128718-87-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 83.6 percent / 6N HCl, dithioethane / ethyl acetate / 1 h

2: 92 percent / Et₃N / dimethylformamide / Ambient temperature

3: H₂ / 5percent Pd/C / dimethylformamide; ethanol / 5 h

4: Et₃N, 1-hydroxybenzotriazole (HOBt), dicyclohexylcarbodiimide (DCCI) / dimethylformamide / 4 °C

5: 64.5 percent / 3N HCl / acetic acid / 0.5 h / Ambient temperature

6: Et₃N, molecular sieve / 1.5 h

7: sodium cyanoborohydride, AcOH / acetone / 1.5 h

With hydrogenchloride; molecular sieve; hydrogen; sodium cyanoborohydride; benzotriazol-1-ol; ethane-1,2-dithiol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; acetic acid; ethyl acetate; N,N-dimethyl-formamide; acetone;

upstream raw materials:

Cbz-D-Phe

methyl (L)-leucinate hydrochloride

N-tert-butoxycarbonyl-D-tryptophyl-L-leucine methyl ester

(S)-2-[(R)-2-Amino-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester; hydrochloride

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