1-cyano-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-enecarboxylic acid

Base Information

• Chemical Name: 1-cyano-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-enecarboxylic acid
• CAS No.: 1449661-13-5
• Molecular Formula: C₄₃H₆₅N₃O₄S
• Molecular Weight: 720.073
• Mol file: 1449661-13-5.mol

Synonyms:1-cyano-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-enecarboxylic acid

Chemical Property of 1-cyano-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-enecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-cyano-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-enecarboxylic acid

There total 14 articles about 1-cyano-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-enecarboxylic 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: 84.0%

ethyl 1-cyano-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 (1449662-25-2) → 1-cyano-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-enecarboxylic acid (1449661-13-5)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; methanol; at 60 ℃; Inert atmosphere;

Reference yield:

Betulinic acid (472-15-1) → 1-cyano-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-enecarboxylic acid (1449661-13-5)

Guidance literature:

Multi-step reaction with 8 steps

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

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

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

4.1: potassium phosphate / acetonitrile / 36 h / 130 °C / Inert atmosphere; Sealed tube

5.1: boron trifluoride diethyl etherate / toluene / 120 h / 20 °C / Inert atmosphere

6.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

6.2: -78 - 20 °C / Inert atmosphere

7.1: sodium carbonate monohydrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 65 °C / Inert atmosphere; Sealed tube

8.1: sodium hydroxide / 1,4-dioxane; methanol / 60 °C / Inert atmosphere

With hydrogenchloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate monohydrate; diphenyl phosphoryl azide; boron trifluoride diethyl etherate; water; potassium hexamethylsilazane; triethylamine; pyridinium chlorochromate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; acetonitrile; 7.1: |Suzuki Coupling;

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) → 1-cyano-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-enecarboxylic acid (1449661-13-5)

Guidance literature:

Multi-step reaction with 7 steps

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

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

3.1: potassium phosphate / acetonitrile / 36 h / 130 °C / Inert atmosphere; Sealed tube

4.1: boron trifluoride diethyl etherate / toluene / 120 h / 20 °C / Inert atmosphere

5.1: potassium hexamethylsilazane / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: sodium carbonate monohydrate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane; water / 2 h / 65 °C / Inert atmosphere; Sealed tube

7.1: sodium hydroxide / 1,4-dioxane; methanol / 60 °C / Inert atmosphere

With hydrogenchloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate monohydrate; boron trifluoride diethyl etherate; water; potassium hexamethylsilazane; pyridinium chlorochromate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; toluene; acetonitrile; 6.1: |Suzuki Coupling;

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

betulin

betulonic aldehyde