(S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester

Base Information

• Chemical Name: (S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester
• CAS No.: 128632-86-0
• Molecular Formula: C₅₁H₆₆N₈O₁₀S
• Molecular Weight: 983.199

Synonyms:(S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester

Chemical Property of (S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester

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Technology Process of (S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester

There total 8 articles about (S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric 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: 44.8%

Z-Glu-D-Phe-Lys-D-Trp-Leu-Met-OMe*HCl (128659-44-9) → (S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester (128632-86-0)

Guidance literature:

With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In N,N-dimethyl-formamide; 1.) 4 deg C, 48 h, 2.) RT, 3 days;

DOI:10.1021/jm00171a033

Reference yield:

N-benzyloxycarbonyl-D-phenylalanyl-L-lysyl(Boc)-D-tryptophyl-L-leucine methyl ester (128633-07-8) → (S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester (128632-86-0)

Guidance literature:

Multi-step reaction with 6 steps

1: H₂ / 5percent Pd-C / ethanol / 5 h

2: dimethylformamide / 16 h

3: 2M aq. NaOH

4: 71.3 percent / 1-hydroxybenzotriazole (HOBt), triethylamine, dicyclohexylcarbodiimide (DCCI) / dimethylformamide / 4 °C

5: 36.3 percent / 3N HCl, acetic acid / 1 h

6: 44.8 percent / dicyclohexylcarbodiimide (DCCI), 1-hydroxybenzotriazole (HOBt), triethylamine / dimethylformamide / 1.) 4 deg C, 48 h, 2.) RT, 3 days

With hydrogenchloride; sodium hydroxide; 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:

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride (2491-18-1) → (S)-2-{(S)-2-[(R)-2-[((2R,5S,14S)-2-Benzyl-14-benzyloxycarbonylamino-3,11,15-trioxo-1,4,10-triaza-cyclopentadecane-5-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester (128632-86-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 71.3 percent / 1-hydroxybenzotriazole (HOBt), triethylamine, dicyclohexylcarbodiimide (DCCI) / dimethylformamide / 4 °C

2: 36.3 percent / 3N HCl, acetic acid / 1 h

3: 44.8 percent / dicyclohexylcarbodiimide (DCCI), 1-hydroxybenzotriazole (HOBt), triethylamine / dimethylformamide / 1.) 4 deg C, 48 h, 2.) RT, 3 days

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

DOI:10.1021/jm00171a033

upstream raw materials:

Z-Glu-D-Phe-Lys-D-Trp-Leu-Met-OMe*HCl

(S)-methyl 2-amino-4-(methylthio)butanoate hydrochloride

Z-Glu(OBu^t)-D-Phe-Lys(Boc)-D-Trp-Leu-OH

Z-Glu(OBu^t)-D-Phe-Lys(Boc)-D-Trp-Leu-OMe

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