(S)-benzyl 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)cyclohex-3-enecarboxylate

Base Information

• Chemical Name: (S)-benzyl 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)cyclohex-3-enecarboxylate
• CAS No.: 1449662-01-4
• Molecular Formula: C₄₃H₆₁NO₂
• Molecular Weight: 623.963

Synonyms:(S)-benzyl 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)cyclohex-3-enecarboxylate

Chemical Property of (S)-benzyl 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)cyclohex-3-enecarboxylate

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Technology Process of (S)-benzyl 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)cyclohex-3-enecarboxylate

There total 16 articles about (S)-benzyl 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)cyclohex-3-enecarboxylate 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:

Betulinic acid (472-15-1) → (S)-benzyl 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)cyclohex-3-enecarboxylate (1449662-01-4)

Guidance literature:

Multi-step reaction with 7 steps

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

2: hydrogenchloride; water / 1,4-dioxane / 15 h / 60 °C / Inert atmosphere

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

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

5: potassium hexamethylsilazane / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere

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

7: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane; water / 6 h / 75 °C / Inert atmosphere; Sealed tube

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; potassium phosphate; diphenyl phosphoryl azide; water; palladium diacetate; potassium hexamethylsilazane; sodium hydrogencarbonate; triethylamine; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

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) → (S)-benzyl 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)cyclohex-3-enecarboxylate (1449662-01-4)

Guidance literature:

Multi-step reaction with 6 steps

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

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

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

4: potassium hexamethylsilazane / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere

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

6: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane; water / 6 h / 75 °C / Inert atmosphere; Sealed tube

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; potassium phosphate; water; palladium diacetate; potassium hexamethylsilazane; sodium hydrogencarbonate; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

Reference yield:

betulonic aldehyde (4439-98-9) → (S)-benzyl 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)cyclohex-3-enecarboxylate (1449662-01-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 2-methyl-but-2-ene; sodium chlorite; sodium dihydrogen phosphate monohydrate / water; tert-butyl alcohol / 2 h / 20 °C / Inert atmosphere

2: diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine / 1,4-dioxane / 16.66 h / 20 - 102 °C / Inert atmosphere

3: hydrogenchloride; water / 1,4-dioxane / 6 h / 20 °C / Inert atmosphere

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

5: potassium hexamethylsilazane / tetrahydrofuran / 2 h / -78 - 20 °C / Inert atmosphere

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

7: potassium phosphate; palladium diacetate; dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane / 1,4-dioxane; water / 6 h / 75 °C / Inert atmosphere; Sealed tube

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; hydrogenchloride; sodium chlorite; potassium phosphate; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; diphenyl phosphoryl azide; water; palladium diacetate; potassium hexamethylsilazane; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; tert-butyl alcohol;

upstream raw materials:

Betulinic acid

(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

(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 hydrochloride

tert-butyl ((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-3aH-cyclopenta[a]chrysen-3a-yl)carbamate

Downstream raw materials:

(S)-benzyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-(aziridin-1-yl)-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)cyclohex-3-enecarboxylate

(S)-benzyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-5a,5b,8,8,11a-pentamethyl-3a-((2-(4-(methylsulfonyl)piperidin-1-yl)ethyl)amino)-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)cyclohex-3-enecarboxylate trifluoroacetate

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