(1aR,2S,5aR,8S,9aR,11R,11aR)-8-(Acetyloxy)-1a,2,3,4,5a,6,7,8,9,9a,10,11-dodecahydro-11-hydroxy-5a,9,9-trimethyl-13-methylene-5H-2,11a-ethanobenzo[5,6]cyclodec[1,2-b]oxirene-5,12-dione

Base Information

• Chemical Name: (1aR,2S,5aR,8S,9aR,11R,11aR)-8-(Acetyloxy)-1a,2,3,4,5a,6,7,8,9,9a,10,11-dodecahydro-11-hydroxy-5a,9,9-trimethyl-13-methylene-5H-2,11a-ethanobenzo[5,6]cyclodec[1,2-b]oxirene-5,12-dione
• CAS No.: 83159-27-7
• Molecular Formula: C₂₂H₃₀O₆
• Molecular Weight: 390.477
• Mol file: 83159-27-7.mol

Synonyms:

Chemical Property of (1aR,2S,5aR,8S,9aR,11R,11aR)-8-(Acetyloxy)-1a,2,3,4,5a,6,7,8,9,9a,10,11-dodecahydro-11-hydroxy-5a,9,9-trimethyl-13-methylene-5H-2,11a-ethanobenzo[5,6]cyclodec[1,2-b]oxirene-5,12-dione

Chemical Property:

• Vapor Pressure: 4.51E-14mmHg at 25°C
• Boiling Point: 543.4°C at 760 mmHg
• Flash Point: 185.8°C
• PSA: 93.20000
• Density: 1.24g/cm³
• LogP: 2.36720

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1aR,2S,5aR,8S,9aR,11R,11aR)-8-(Acetyloxy)-1a,2,3,4,5a,6,7,8,9,9a,10,11-dodecahydro-11-hydroxy-5a,9,9-trimethyl-13-methylene-5H-2,11a-ethanobenzo[5,6]cyclodec[1,2-b]oxirene-5,12-dione

There total 15 articles about (1aR,2S,5aR,8S,9aR,11R,11aR)-8-(Acetyloxy)-1a,2,3,4,5a,6,7,8,9,9a,10,11-dodecahydro-11-hydroxy-5a,9,9-trimethyl-13-methylene-5H-2,11a-ethanobenzo[5,6]cyclodec[1,2-b]oxirene-5,12-dione 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: 70.0%

shikoccin (73211-11-7) → epoxyshikoccin (83159-27-7)

Guidance literature:

With disodium hydrogenphosphate; trifluoroacetic anhydride; In dichloromethane; at 0 - 20 ℃; for 6h; Inert atmosphere;

DOI:10.1002/anie.202104410

Reference yield: 6.4%

shikoccin (73211-11-7) → epoxyshikoccin (83159-27-7) + Acetic acid (4R,6S,9R,13R)-5,5,9-trimethyl-14-methylene-2,10,15-trioxo-tricyclo[11.2.1.04,9]hexadec-1(16)-en-6-yl ester (99432-98-1) + C22H28O6 (90663-21-1)

Guidance literature:

With jones reagent; In acetone; for 3h; ice-cooling;

Reference yield:

C18H31N3O5 → epoxyshikoccin (83159-27-7)

Guidance literature:

Multi-step reaction with 11 steps

1.1: lead(IV) tetraacetate / dichloromethane / 1 h / 0 °C / Inert atmosphere

2.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 1 h / 80 °C / Inert atmosphere

2.2: Inert atmosphere

3.1: tetrahydrofuran / 4 h / Inert atmosphere; Irradiation

3.2: 0.5 h / 20 °C / Inert atmosphere

4.1: potassium pyrophosphate; 1,1,1,3',3',3'-hexafluoro-propanol; bis-[(trifluoroacetoxy)iodo]benzene / 0.5 h / 0 °C

5.1: LiAlH(Ot-Bu)3 / tetrahydrofuran / 0.5 h / 0 °C / Inert atmosphere

5.2: 0.5 h / 50 °C / Inert atmosphere

6.1: lithium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -78 °C / Inert atmosphere

6.2: 0.5 h / 20 °C / Inert atmosphere

6.3: 0.08 h / 20 °C / Inert atmosphere

7.1: potassium tert-butylate; diisobutylaluminium hydride / tetrahydrofuran; toluene / 1.5 h / 0 °C / Inert atmosphere

7.2: 0.5 h / 20 °C / Inert atmosphere

7.3: 72 h / 0 °C / Irradiation

8.1: triethylamine; triethylsilyl chloride / dichloromethane / 0.5 h / 20 °C / Inert atmosphere

8.2: Inert atmosphere

9.1: triethylamine / toluene / 0.17 h / 80 °C / Inert atmosphere

9.2: 2 h / 80 °C / Inert atmosphere

10.1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / 20686.5 Torr

10.2: 3 h / 35 °C

11.1: disodium hydrogenphosphate; trifluoroacetic anhydride / dichloromethane / 6 h / 0 - 20 °C / Inert atmosphere

With potassium pyrophosphate; disodium hydrogenphosphate; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); triethylsilyl chloride; 1,1,1,3',3',3'-hexafluoro-propanol; LiAlH(Ot-Bu)3; 5%-palladium/activated carbon; potassium tert-butylate; hydrogen; lead(IV) tetraacetate; diisobutylaluminium hydride; triethylamine; trifluoroacetic anhydride; bis-[(trifluoroacetoxy)iodo]benzene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; toluene;

DOI:10.1002/anie.202104410

upstream raw materials:

shikoccin

shikoccidin

Downstream raw materials:

O-methylepoxyshikoccin