methyl 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: methyl 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.: 1449661-63-5
• Molecular Formula: C₃₇H₅₇NO₂
• Molecular Weight: 547.865
• Mol file: 1449661-63-5.mol

Synonyms:methyl 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 methyl 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:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 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 13 articles about methyl 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: 32.7%

4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3-cyclohexene-1-carboxylic acid methyl ester (151075-20-6) + (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) → methyl 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 (1449661-63-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate monohydrate; In 1,4-dioxane; water; at 85 ℃; for 20.5h; Inert atmosphere; Sealed tube;

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) → methyl 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 (1449661-63-5)

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: sodium carbonate monohydrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 20.5 h / 85 °C / Inert atmosphere; Sealed tube

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate monohydrate; water; potassium hexamethylsilazane; sodium hydrogencarbonate; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water;

Reference yield:

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol (1072913-62-2) → methyl 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 (1449661-63-5)

Guidance literature:

Multi-step reaction with 8 steps

1: triethylamine; oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.42 h / -15 °C / Inert atmosphere

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

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

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

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

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

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

8: sodium carbonate monohydrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 20.5 h / 85 °C / Inert atmosphere; Sealed tube

With hydrogenchloride; sodium chlorite; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium dihydrogen phosphate monohydrate; 2-methyl-but-2-ene; oxalyl dichloride; sodium carbonate monohydrate; diphenyl phosphoryl azide; water; potassium hexamethylsilazane; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; tert-butyl alcohol;

upstream raw materials:

(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,11aR,11bR,13aR,13bR)-3a-((tert-butoxycarbonyl)amino)-5 a,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

betulin

(1R,3aS,5aR,5bR,7aR,9S,11aR,11bR,13bR)-3a-(hydroxymethyl)-5a,5b,8,8,11a-pentamethyl-1-(prop-1-en-2-yl)icosahydro-1H-cyclopenta[a]chrysen-9-ol

Downstream raw materials:

methyl 4-((1R,3aS,5aR,5bR,7aR,11aS,11bR,13aR,13bR)-3a-((2-(1,1-dioxidothiomorpholino)ethyl)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