(1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid

Base Information

• Chemical Name: (1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid
• CAS No.: 1616704-81-4
• Molecular Formula: C₅₁H₇₁N₃O₅
• Molecular Weight: 806.142
• Mol file: 1616704-81-4.mol

Synonyms:(1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid

Chemical Property of (1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid

There total 17 articles about (1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic 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:

Reference yield: 43.5%

1-benzyl 3-((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl) (1S,3R)-2,2-dimethylcyclobutane-1,3-dicarboxylate (1616705-33-9) → (1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid (1616704-81-4)

Guidance literature:

With palladium 10% on activated carbon; ammonium formate; In methanol; ethyl acetate; at 20 ℃; for 2h;

Reference yield:

(+)-cis-pinononoic acid (22571-78-4) → (1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid (1616704-81-4)

Guidance literature:

Multi-step reaction with 6 steps

1: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C / Cooling with ice

2: sodium hydroxide; water; bromine / 13 h / 0 - 20 °C

3: sodium carbonate; tetrabutylammomium bromide / dichloromethane; water / 12 h / 0 - 20 °C

4: hydrogenchloride / 1,4-dioxane / 4 h / 0 - 20 °C

5: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 0 - 20 °C

6: ammonium formate; palladium 10% on activated carbon / methanol; ethyl acetate / 2 h / 20 °C

With hydrogenchloride; dmap; palladium 10% on activated carbon; tetrabutylammomium bromide; water; bromine; ammonium formate; sodium carbonate; dicyclohexyl-carbodiimide; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate;

Reference yield:

Verbenone (18309-32-5) → (1S,3R)-2,2-dimethyl-3-((((1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((S)-2-(5-phenyl-1H-imidazol-2-yl)pyrrolidine-1-carbonyl)-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-yl)oxy)carbonyl)cyclobutane-1-carboxylic acid (1616704-81-4)

Guidance literature:

Multi-step reaction with 7 steps

1: water; potassium permanganate / acetone / 3 h / 0 °C

2: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 20 °C / Cooling with ice

3: sodium hydroxide; water; bromine / 13 h / 0 - 20 °C

4: sodium carbonate; tetrabutylammomium bromide / dichloromethane; water / 12 h / 0 - 20 °C

5: hydrogenchloride / 1,4-dioxane / 4 h / 0 - 20 °C

6: dmap; dicyclohexyl-carbodiimide / dichloromethane / 12 h / 0 - 20 °C

7: ammonium formate; palladium 10% on activated carbon / methanol; ethyl acetate / 2 h / 20 °C

With hydrogenchloride; dmap; potassium permanganate; palladium 10% on activated carbon; tetrabutylammomium bromide; water; bromine; ammonium formate; sodium carbonate; dicyclohexyl-carbodiimide; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; ethyl acetate; acetone;

upstream raw materials:

(+)-cis-pinononoic acid

Verbenone

tert-butyl (1R,3S)-3-acetyl-2,2-dimethylcyclobutane-1-carboxylate

(1S,3R)-3-(tert-butoxycarbonyl)-2,2-dimethylcyclobutane-1-carboxylic acid