ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate

Base Information

• Chemical Name: ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate
• CAS No.: 1622929-51-4
• Molecular Formula: C₃₉H₆₃NO₂
• Molecular Weight: 577.935

Synonyms:ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate

Chemical Property of ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate

There total 13 articles about ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate 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: 76.0%

(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate (1392314-08-7) + ethyl 4-methylidenecyclohexanecarboxylate (145576-28-9) → ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate (1622929-51-4)

Guidance literature:

ethyl 4-methylidenecyclohexanecarboxylate; With 9-bora-bicyclo[3.3.1]nonane; In tetrahydrofuran; at 0 - 20 ℃; for 2h; Cooling with ice; Inert atmosphere;

(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate; With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; phosphoric acid; In tetrahydrofuran; 1,4-dioxane; toluene; at 85 ℃; for 18.5h; Inert atmosphere;

Reference yield:

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13aR,13bR)-3a-isocyanato-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol (672958-04-2) → ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate (1622929-51-4)

Guidance literature:

Multi-step reaction with 6 steps

1.1: pyridinium chlorochromate / dichloromethane / 6.75 h / 20 °C / Inert atmosphere

2.1: hydrogenchloride / 1,4-dioxane / 15.5 h / 60 °C / Inert atmosphere

3.1: sodium hydroxide / 1,4-dioxane; water; dichloromethane; methanol / 28.5 h / 20 °C / Inert atmosphere

4.1: potassium hexamethylsilazane / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

4.2: 5 h / -78 °C / Inert atmosphere

5.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

6.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C / Cooling with ice; Inert atmosphere

6.2: 18.5 h / 85 °C / Inert atmosphere

With hydrogenchloride; potassium hexamethylsilazane; 9-bora-bicyclo[3.3.1]nonane; pyridinium chlorochromate; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water;

Reference yield:

Betulinic acid (472-15-1) → ethyl 4-(((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl)methyl)cyclohexanecarboxylate (1622929-51-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: triethylamine; diphenyl phosphoryl azide / 1,4-dioxane / 26 h / Reflux; Inert atmosphere

2.1: hydrogenchloride / 1,4-dioxane / 15 h / 60 °C / Inert atmosphere

3.1: sodium hydrogencarbonate / 1,4-dioxane; water / 16 h / 20 °C / Inert atmosphere

4.1: pyridinium chlorochromate / dichloromethane / 6 h / 20 °C / Inert atmosphere

5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.33 h / -78 °C / Inert atmosphere

5.2: 5 h / -78 °C / Inert atmosphere

6.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C / Inert atmosphere

7.1: 9-bora-bicyclo[3.3.1]nonane / tetrahydrofuran / 2 h / 0 - 20 °C / Cooling with ice; Inert atmosphere

7.2: 18.5 h / 85 °C / Inert atmosphere

With hydrogenchloride; diphenyl phosphoryl azide; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; 9-bora-bicyclo[3.3.1]nonane; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

upstream raw materials:

(1R,3aS,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-3a-amino-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)-2,3,3a,4,5,5a,5b,6,7,7a,8,11,11a,11b,12,13,13a,13b-octadecahydro-1H-cyclopenta[a]chrysen-9-yl trifluoromethanesulfonate

ethyl 4-methylidenecyclohexanecarboxylate

ethyl 4-oxocyclohexane-1-carboxylate

Betulinic acid

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