Technology Process of methyl (3R,6R,9S,12S,14E,16R,18S)-6-<(2-bromo-1H-indol-3-yl)methyl>-18-benzoyloxy-3-<4-(tert-butyldimethylsilyloxy)phenyl>-7,9,12,14,16-pentamethyl-5,8,11-trioxo-4,7,10-triazanonadeca-14-enoate
There total 20 articles about methyl (3R,6R,9S,12S,14E,16R,18S)-6-<(2-bromo-1H-indol-3-yl)methyl>-18-benzoyloxy-3-<4-(tert-butyldimethylsilyloxy)phenyl>-7,9,12,14,16-pentamethyl-5,8,11-trioxo-4,7,10-triazanonadeca-14-enoate 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:
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161925-58-2
methyl (3R,6R,9S,12S,14E,16R,18S)-6-<(2-bromo-1H-indol-3-yl)methyl>-18-benzoyloxy-3-<4-(tert-butyldimethylsilyloxy)phenyl>-7,9,12,14,16-pentamethyl-5,8,11-trioxo-4,7,10-triazanonadeca-14-enoate
- Guidance literature:
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Multi-step reaction with 6 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
6: DCC, HOBT / CH2Cl2 / 1.) -20 deg C, 30 min, 2.) 4 deg C, 40 h 78 percent
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
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161925-58-2
methyl (3R,6R,9S,12S,14E,16R,18S)-6-<(2-bromo-1H-indol-3-yl)methyl>-18-benzoyloxy-3-<4-(tert-butyldimethylsilyloxy)phenyl>-7,9,12,14,16-pentamethyl-5,8,11-trioxo-4,7,10-triazanonadeca-14-enoate
- Guidance literature:
-
Multi-step reaction with 6 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
6: DCC, HOBT / CH2Cl2 / 1.) -20 deg C, 30 min, 2.) 4 deg C, 40 h 78 percent
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
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-
161925-58-2
methyl (3R,6R,9S,12S,14E,16R,18S)-6-<(2-bromo-1H-indol-3-yl)methyl>-18-benzoyloxy-3-<4-(tert-butyldimethylsilyloxy)phenyl>-7,9,12,14,16-pentamethyl-5,8,11-trioxo-4,7,10-triazanonadeca-14-enoate
- Guidance literature:
-
Multi-step reaction with 5 steps
1: 1.) BuLi / 1.) THF, hexane, 0 deg C, 15 min, 2.) THF, -78 deg C, 20 min
2: 90 percent / H2 / 5percent PdC / tetrahydrofuran; acetic acid / 21 h / 33602700 Torr / Ambient temperature
3: 89 percent / HOBT, DCC / tetrahydrofuran / 15 h / Ambient temperature
4: 73 percent / TBSOTf, 2,6-lutidine / CH2Cl2 / 2 h / 0 °C
5: DCC, HOBT / CH2Cl2 / 1.) -20 deg C, 30 min, 2.) 4 deg C, 40 h 78 percent
With
2,6-dimethylpyridine; n-butyllithium; t-butyldimethylsiyl triflate; hydrogen; benzotriazol-1-ol; dicyclohexyl-carbodiimide;
dipyridinium dichromate;
In
tetrahydrofuran; dichloromethane; acetic acid;
DOI:10.1055/s-1995-3870
