(S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester

Base Information

• Chemical Name: (S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester
• CAS No.: 128632-79-1
• Molecular Formula: C₄₆H₅₇N₇O₉S
• Molecular Weight: 884.066

Synonyms:(S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester

Chemical Property of (S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester

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Technology Process of (S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester

There total 5 articles about (S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid 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: 26.0%

Z-Cys(CH2COOH)-D-Phe-Lys-D-Trp-Leu-OMe (128633-22-7) → (S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester (128632-79-1)

Guidance literature:

With diphenyl phosphoryl azide; In N,N-dimethyl-formamide;

DOI:10.1021/jm00171a033

Reference yield:

N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(Boc)-D-tryptophyl-L-leucine methyl ester (128633-07-8) → (S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester (128632-79-1)

Guidance literature:

Multi-step reaction with 4 steps

1: H₂ / 5percent Pd-C / ethanol / 5 h

2: 68 percent / dicyclohexylcarbodiimide (DCCI), 1-hydroxybenzotriazole (HOBt), triethylamine / dimethylformamide / 1.) 4 deg C, 48 h, 2.) RT, 3 days

3: 66.2 percent / 2.5N HCl, acetic acid / 0.5 h / Ambient temperature

4: 26 percent / diphenyl phosphorazidate / dimethylformamide

With hydrogenchloride; diphenyl phosphoryl azide; hydrogen; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In ethanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00171a033

Reference yield:

Z-Cys(CH2COOBut) (128633-20-5) → (S)-2-[(R)-2-[((9S,12R,15R)-12-Benzyl-15-benzyloxycarbonylamino-3,11,14-trioxo-1-thia-4,10,13-triaza-cyclohexadecane-9-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoic acid methyl ester (128632-79-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 68 percent / dicyclohexylcarbodiimide (DCCI), 1-hydroxybenzotriazole (HOBt), triethylamine / dimethylformamide / 1.) 4 deg C, 48 h, 2.) RT, 3 days

2: 66.2 percent / 2.5N HCl, acetic acid / 0.5 h / Ambient temperature

3: 26 percent / diphenyl phosphorazidate / dimethylformamide

With hydrogenchloride; diphenyl phosphoryl azide; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide;

DOI:10.1021/jm00171a033

upstream raw materials:

Z-Cys(CH₂COOH)-D-Phe-Lys-D-Trp-Leu-OMe

Z-Cys(CH₂COOBu^t)

Z-Cys(CH₂COOBu^t)-D-Phe-Lys(Boc)-D-Trp-Leu-OMe

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

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