andrographolide

Base Information

• Chemical Name: andrographolide
• CAS No.: 142037-79-4
• Molecular Formula: C₂₀H₃₀O₅
• Molecular Weight: 350.455
• Mol file: 142037-79-4.mol

Synonyms:

Chemical Property of andrographolide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of andrographolide

There total 17 articles about andrographolide 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: 92.0%

(S,E)-3-(2-((1R,4aS,5R,6R,8aS)-5,8a-dimethyl-2-methylene-6-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)decahydronaphthalen-1-yl)ethylidene)-4-hydroxydihydrofuran-2(3H)-one → andrographolide (142037-79-4,5508-58-7)

Guidance literature:

With pyridine; pyridine hydrogenfluoride; In tetrahydrofuran; at 0 - 20 ℃; for 34h; Inert atmosphere;

DOI:10.1002/anie.202011363

Reference yield:

((4aS,5R,6R,8aR)-5,8a-dimethyl-6-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)-3,4,4a,5,6,7,8,8a-octahydronaphthalene-1,2-diyl)dimethanol → andrographolide (142037-79-4,5508-58-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: di-isopropyl azodicarboxylate; triphenylphosphine; 2-nitrobenzenesulfonyl hydrazide / tetrahydrofuran / 7.5 h / -30 - 25 °C / Inert atmosphere

2.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

3.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere

3.2: 0.08 h / -78 - 0 °C / Inert atmosphere

4.1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium carbonate; tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 15 h / 80 °C / Inert atmosphere; Schlenk technique

5.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 34 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; di-isopropyl azodicarboxylate; 2-nitrobenzenesulfonyl hydrazide; iodine; tert.-butyl lithium; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium carbonate; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; diethyl ether; pentane;

DOI:10.1002/anie.202011363

Reference yield:

((1R,4aS,5R,6R,8aR)-5,8a-dimethyl-2-methylene-6-((triisopropylsilyl)oxy)-5-(((triisopropylsilyl)oxy)methyl)decahydronaphthalen-1-yl)methanol → andrographolide (142037-79-4,5508-58-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: triphenylphosphine; 1H-imidazole; iodine / tetrahydrofuran / 24 h / 0 - 20 °C / Inert atmosphere

2.1: tert.-butyl lithium / diethyl ether; pentane / 1 h / -78 °C / Inert atmosphere

2.2: 0.08 h / -78 - 0 °C / Inert atmosphere

3.1: triethylamine; palladium diacetate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; sodium carbonate; tetra-(n-butyl)ammonium iodide / 1,4-dioxane / 15 h / 80 °C / Inert atmosphere; Schlenk technique

4.1: pyridine hydrogenfluoride; pyridine / tetrahydrofuran / 34 h / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; iodine; tert.-butyl lithium; palladium diacetate; tetra-(n-butyl)ammonium iodide; sodium carbonate; pyridine hydrogenfluoride; triethylamine; triphenylphosphine; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; diethyl ether; pentane;

DOI:10.1002/anie.202011363

upstream raw materials:

geraniol

Downstream raw materials:

14-deoxy-11,12-didehydroandrographolide

14-deoxy-12-methoxy-andrographolide

19-Tr-andrographolide

C₂₉H₃₆O₇

Refernces