Technology Process of 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1R,3S)-3-(benzyloxycarbonyl)-2,2-dimethylcyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid
There total 15 articles about 4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1R,3S)-3-(benzyloxycarbonyl)-2,2-dimethylcyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid 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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1261254-61-8
(1S,3R)-benzyl 3-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-9-hydroxy-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysene-3a-carboxamido)-2,2-dimethylcyclobutanecarboxylate
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1261253-61-5
4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1R,3S)-3-(benzyloxycarbonyl)-2,2-dimethylcyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid
- Guidance literature:
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With
pyridine; dmap;
for 20h;
Reflux;
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1261253-61-5
4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1R,3S)-3-(benzyloxycarbonyl)-2,2-dimethylcyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid
- Guidance literature:
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Multi-step reaction with 11 steps
1.1: sodium periodate; water / ruthenium(III) trichloride hydrate / tetrachloromethane; acetonitrile / 12 h / 0 - 20 °C
2.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
3.1: sodium azide; methanesulfonic acid / 1,2-dimethoxyethane / 48 h / -45 - 20 °C
4.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 1 h / 20 °C
5.1: hydrogenchloride; water / 12 h / Reflux
5.2: pH 8 - 9
5.3: 16 h / 0 - 20 °C
6.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
7.1: dichloromethane / 0.5 h / 0 - 20 °C
8.1: triethylamine / dichloromethane / 16 h / -5 - 20 °C
9.1: sodium hydroxide; water / tetrahydrofuran; methanol / 6 h / 0 - 20 °C
10.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
11.1: dmap; pyridine / 20 h / Reflux
With
pyridine; hydrogenchloride; dmap; sodium periodate; sodium azide; methanesulfonic acid; water; hydrogen; caesium carbonate; triethylamine; sodium hydroxide;
ruthenium(III) trichloride hydrate; palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; tetrachloromethane; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile;
3.1: Schmidt Rearrangement;
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1261253-61-5
4-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-((1R,3S)-3-(benzyloxycarbonyl)-2,2-dimethylcyclobutylcarbamoyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yloxy)-2,2-dimethyl-4-oxobutanoic acid
- Guidance literature:
-
Multi-step reaction with 10 steps
1.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
2.1: sodium azide; methanesulfonic acid / 1,2-dimethoxyethane / 48 h / -45 - 20 °C
3.1: hydrogen / palladium 10% on activated carbon / ethyl acetate / 1 h / 20 °C
4.1: hydrogenchloride; water / 12 h / Reflux
4.2: pH 8 - 9
4.3: 16 h / 0 - 20 °C
5.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
6.1: dichloromethane / 0.5 h / 0 - 20 °C
7.1: triethylamine / dichloromethane / 16 h / -5 - 20 °C
8.1: sodium hydroxide; water / tetrahydrofuran; methanol / 6 h / 0 - 20 °C
9.1: caesium carbonate / N,N-dimethyl-formamide / 2 h / 0 - 20 °C
10.1: dmap; pyridine / 20 h / Reflux
With
pyridine; hydrogenchloride; dmap; sodium azide; methanesulfonic acid; water; hydrogen; caesium carbonate; triethylamine; sodium hydroxide;
palladium 10% on activated carbon;
In
tetrahydrofuran; methanol; 1,2-dimethoxyethane; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
2.1: Schmidt Rearrangement;