(S)-2-{(S)-2-[(R)-2-[((4R,7R,10R)-7-Benzyl-10-tert-butoxycarbonylamino-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-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-[((4R,7R,10R)-7-Benzyl-10-tert-butoxycarbonylamino-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester
• CAS No.: 128632-78-0
• Molecular Formula: C₄₃H₅₉N₇O₉S₃
• Molecular Weight: 914.181

Synonyms:

Chemical Property of (S)-2-{(S)-2-[(R)-2-[((4R,7R,10R)-7-Benzyl-10-tert-butoxycarbonylamino-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-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-[((4R,7R,10R)-7-Benzyl-10-tert-butoxycarbonylamino-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester

There total 4 articles about (S)-2-{(S)-2-[(R)-2-[((4R,7R,10R)-7-Benzyl-10-tert-butoxycarbonylamino-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-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: 13.7%

Boc-Cys(Acm)-D-Phe-Cys(Acm)-D-Trp-Leu-Met-OMe (128633-19-2) → (S)-2-{(S)-2-[(R)-2-[((4R,7R,10R)-7-Benzyl-10-tert-butoxycarbonylamino-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester (128632-78-0)

Guidance literature:

With iodine; In methanol; N,N-dimethyl-formamide; for 0.1h;

DOI:10.1021/jm00171a033

Reference yield:

Met-OMe (10332-17-9,874219-77-9) → (S)-2-{(S)-2-[(R)-2-[((4R,7R,10R)-7-Benzyl-10-tert-butoxycarbonylamino-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester (128632-78-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 13.7 percent / iodine / dimethylformamide; methanol / 0.1 h

With iodine; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00171a033

Reference yield:

Boc-Cys(Acm)-D-Phe-Cys(Acm)-D-Trp-Leu-OH → (S)-2-{(S)-2-[(R)-2-[((4R,7R,10R)-7-Benzyl-10-tert-butoxycarbonylamino-6,9-dioxo-1,2-dithia-5,8-diaza-cycloundecane-4-carbonyl)-amino]-3-(1H-indol-3-yl)-propionylamino]-4-methyl-pentanoylamino}-4-methylsulfanyl-butyric acid methyl ester (128632-78-0)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 13.7 percent / iodine / dimethylformamide; methanol / 0.1 h

With iodine; benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00171a033

upstream raw materials:

Boc-Cys(Acm)-D-Phe-Cys(Acm)-D-Trp-Leu-Met-OMe

Met-OMe

N-tert-butoxycarbonyl-L-cysteinyl(Acm)-D-phenylalanyl-L-cysteinyl(Acm)-D-tryptophyl-L-leucine methyl ester

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