methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate

Base Information

Chemical Name:methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate
CAS No.:161925-44-6
Molecular Formula:C₃₁H₄₃BrN₄O₅Si
Molecular Weight:659.696
Hs Code.:

Synonyms:methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate

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Chemical Property of methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate

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Technology Process of methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate

There total 12 articles about methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate 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: 73.0%

: 161925-57-1
methyl (3R,6R,9S)-9-(tert-butoxycarbonylamino)-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate

: 161925-44-6
methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate

Guidance literature:: With 2,6-dimethylpyridine; t-butyldimethylsiyl triflate; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1055/s-1995-3870

Reference yield:

: 3943-97-3
methyl 4-hydroxycinnamate

: 161925-44-6
methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / imidazole / dimethylformamide / 1 h / 0 °C

2: 1.) BuLi / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, -78 deg C, 20 min

3: 90 percent / H₂ / 5percent PdC / tetrahydrofuran; acetic acid / 21 h / 33602700 Torr / Ambient temperature

4: 89 percent / HOBT, DCC / tetrahydrofuran / 15 h / Ambient temperature

5: 73 percent / TBSOTf, 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; t-butyldimethylsiyl triflate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; dipyridinium dichromate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1055/s-1995-3870

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 161925-44-6
methyl (3R,6R,9S)-9-amino-7-methyl-6-<(2-bromo-1H-indol-3-yl)methyl>-3-<4-(tert-butyldimethylsilyloxy)phenyl>-5,8-dioxo-4,7-diazadecanoate

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / imidazole / dimethylformamide / 1 h / 0 °C

2: 1.) BuLi / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, -78 deg C, 20 min

3: 90 percent / H₂ / 5percent PdC / tetrahydrofuran; acetic acid / 21 h / 33602700 Torr / Ambient temperature

4: 89 percent / HOBT, DCC / tetrahydrofuran / 15 h / Ambient temperature

5: 73 percent / TBSOTf, 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; n-butyllithium; t-butyldimethylsiyl triflate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide; dipyridinium dichromate; In tetrahydrofuran; dichloromethane; acetic acid; N,N-dimethyl-formamide;
DOI:10.1055/s-1995-3870