armillarivin

Base Information

• Chemical Name: armillarivin
• CAS No.: 135247-97-1
• Molecular Formula: C₂₃H₂₈O₅
• Molecular Weight: 384.472
• Mol file: 135247-97-1.mol

Synonyms:Benzoicacid, 2,4-dihydroxy-6-methyl-,3-formyl-2,2a,4a,5,6,7,7a,7b-octahydro-6,6,7b-trimethyl-1H-cyclobut[e]inden-2-ylester, (2a,2ab,4aa,7aa,7bb)-(+)-; Armillarivin

Chemical Property of armillarivin

Chemical Property:

• Vapor Pressure: 2.05E-12mmHg at 25°C
• Boiling Point: 543.3°Cat760mmHg
• Flash Point: 185.8°C
• PSA: 83.83000
• Density: 1.27g/cm³
• LogP: 4.14910

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of armillarivin

There total 22 articles about armillarivin 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:

(3aR,4S,4aS,7aR,8R,8aS)-3a,4a,5,6,7,7a,8,8a-octahydro-2,2,4,6,6-pentamethyl-4,8-etheno-4H-indeno[5,6-d]-1,3-dioxole (499121-60-7) → (+)-armillarivin (135247-97-1)

Guidance literature:

Multi-step reaction with 15 steps

1.1: dimethylsulfide borane complex / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

1.2: 20 h / 20 °C

2.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 16 h / 0 - 20 °C

3.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

3.2: 2 h / 0 - 20 °C / Inert atmosphere

4.1: triethylamine; lithium chloride / tetrahydrofuran / 0.08 h / Inert atmosphere

4.2: 16 h / Inert atmosphere; Reflux

5.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

7.1: Dowex-50 (H⁺-form) / water; methanol / 16 h / Reflux

8.1: 1H-imidazole / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

9.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 1 h / 0 °C

10.1: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

11.1: samarium diiodide / tetrahydrofuran; methanol / 0.08 h / -78 °C / Inert atmosphere

12.1: dichloromethane / 1.5 h / 0 °C / Irradiation; Schlenk technique; High pressure

13.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

14.1: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran; N,N-dimethyl-formamide / 20 h / 60 °C / Inert atmosphere

15.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 16 h / 0 - 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; samarium diiodide; dimethylsulfide borane complex; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ol400583c

Reference yield:

C19H28O3S2 → (+)-armillarivin (135247-97-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride / toluene / 18 h / 100 °C / Reflux

2.1: dimethylsulfide borane complex / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere

2.2: 20 h / 20 °C

3.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 16 h / 0 - 20 °C

4.1: lithium hexamethyldisilazane / tetrahydrofuran / 1.5 h / 0 °C / Inert atmosphere

4.2: 2 h / 0 - 20 °C / Inert atmosphere

5.1: triethylamine; lithium chloride / tetrahydrofuran / 0.08 h / Inert atmosphere

5.2: 16 h / Inert atmosphere; Reflux

6.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

7.1: lithium aluminium tetrahydride / tetrahydrofuran / 1.17 h / -78 °C / Inert atmosphere

8.1: Dowex-50 (H⁺-form) / water; methanol / 16 h / Reflux

9.1: 1H-imidazole / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

10.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 1 h / 0 °C

11.1: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

12.1: samarium diiodide / tetrahydrofuran; methanol / 0.08 h / -78 °C / Inert atmosphere

13.1: dichloromethane / 1.5 h / 0 °C / Irradiation; Schlenk technique; High pressure

14.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

15.1: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran; N,N-dimethyl-formamide / 20 h / 60 °C / Inert atmosphere

16.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 16 h / 0 - 20 °C

With 1H-imidazole; dmap; lithium aluminium tetrahydride; samarium diiodide; 2,2'-azobis(isobutyronitrile); dimethylsulfide borane complex; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: |Barton-McCombie Deoxygenation;

DOI:10.1021/ol400583c

Reference yield:

C19H28O5 (1429059-91-5) → (+)-armillarivin (135247-97-1)

Guidance literature:

Multi-step reaction with 12 steps

1.1: sodium hydride / tetrahydrofuran; mineral oil / 1 h / 0 °C / Inert atmosphere

1.2: 18 h / 4 °C / Inert atmosphere

2.1: methyllithium; copper(l) iodide / diethyl ether / 3 h / -35 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane / 1 h / -78 °C / Inert atmosphere

4.1: Dowex-50 (H⁺-form) / water; methanol / 16 h / Reflux

5.1: 1H-imidazole / dichloromethane / 16 h / 0 - 20 °C / Inert atmosphere

6.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 1 h / 0 °C

7.1: triethylamine; dmap / dichloromethane / 16 h / 20 °C / Inert atmosphere

8.1: samarium diiodide / tetrahydrofuran; methanol / 0.08 h / -78 °C / Inert atmosphere

9.1: dichloromethane / 1.5 h / 0 °C / Irradiation; Schlenk technique; High pressure

10.1: lithium aluminium tetrahydride / tetrahydrofuran / 1 h / -78 °C / Inert atmosphere

11.1: dicyclohexyl-carbodiimide; dmap / tetrahydrofuran; N,N-dimethyl-formamide / 20 h / 60 °C / Inert atmosphere

12.1: toluene-4-sulfonic acid; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy / dichloromethane / 16 h / 0 - 20 °C

With 1H-imidazole; dmap; copper(l) iodide; lithium aluminium tetrahydride; samarium diiodide; 4-acetylamino-2,2,6,6-tetramethyl-1-piperidinoxy; methyllithium; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ol400583c

upstream raw materials:

(3aR,4S,4aS,7aR,8R,8aS)-3a,4a,5,6,7,7a,8,8a-octahydro-2,2,4,6,6-pentamethyl-4,8-etheno-4H-indeno[5,6-d]-1,3-dioxole

C₁₇H₂₈O₃

C₁₇H₂₈O₃

C₁₇H₂₆O₃

Refernces