(3S,4aR,6R,10R,13aR)-3-Acetoxy-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione

Base Information

Chemical Name:(3S,4aR,6R,10R,13aR)-3-Acetoxy-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione
CAS No.:73211-11-7
Molecular Formula:C22H30 O5
Molecular Weight:0
Hs Code.:
Mol file:73211-11-7.mol

(3S,4aR,6R,10R,13aR)-3-Acetoxy-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione

Synonyms:10,7-Metheno-7H-benzocycloundecene-8,13-dione,3-(acetyloxy)-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-,(3S,4aR,6R,10R,13aR)- (9CI); 10,7-Metheno-7H-benzocycloundecene-8,13-dione,3-(acetyloxy)-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-,[3S-(3R*,4aS*,6S*,10S*,13aS*)]-; NSC 302979; Shikoccin

Suppliers and Price of (3S,4aR,6R,10R,13aR)-3-Acetoxy-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4aR,6R,10R,13aR)-3-Acetoxy-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione

Chemical Property:

Vapor Pressure:3.01E-13mmHg at 25°C
Boiling Point:525.7°C at 760 mmHg
Flash Point:178.4°C
PSA：80.67000
Density:1.17g/cm³
LogP:3.15600

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:: SDS file from LookChem

Useful:

Technology Process of (3S,4aR,6R,10R,13aR)-3-Acetoxy-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-dione

There total 13 articles about (3S,4aR,6R,10R,13aR)-3-Acetoxy-1,2,3,4,4a,5,6,9,10,11,12,13a-dodecahydro-6-hydroxy-4,4,13a-trimethyl-9-methylene-10,7-metheno-7H-benzocycloundecene-8,13-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: 80.0%

: C₃₁H₄₀O₈S

: 73211-11-7
shikoccin

Guidance literature:: C₃₁H₄₀O₈S; With 5%-palladium/activated carbon; hydrogen; In methanol; at 20 ℃; for 12h; under 20686.5 Torr;

With toluene-4-sulfonic acid; In methanol; at 35 ℃; for 3h;
DOI:10.1002/anie.202104410

Reference yield:

: C₁₈H₃₁N₃O₅

: 73211-11-7
shikoccin

Guidance literature:: Multi-step reaction with 10 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

With potassium pyrophosphate; 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; bis-[(trifluoroacetoxy)iodo]benzene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; tetrachloromethane; dichloromethane; toluene;
DOI:10.1002/anie.202104410

Reference yield:

: C₁₇H₂₈O₅

: 73211-11-7
shikoccin

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium acetate / ethanol; water / 1 h / 20 °C / Inert atmosphere

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

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

3.2: Inert atmosphere

4.1: tetrahydrofuran / 4 h / Inert atmosphere; Irradiation

4.2: 0.5 h / 20 °C / Inert atmosphere

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

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

6.2: 0.5 h / 50 °C / Inert atmosphere

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

7.2: 0.5 h / 20 °C / Inert atmosphere

7.3: 0.08 h / 20 °C / Inert atmosphere

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

8.2: 0.5 h / 20 °C / Inert atmosphere

8.3: 72 h / 0 °C / Irradiation

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

9.2: Inert atmosphere

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

10.2: 2 h / 80 °C / Inert atmosphere

11.1: 5%-palladium/activated carbon; hydrogen / methanol / 12 h / 20 °C / 20686.5 Torr

11.2: 3 h / 35 °C

With potassium pyrophosphate; 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; sodium acetate; lead(IV) tetraacetate; diisobutylaluminium hydride; triethylamine; bis-[(trifluoroacetoxy)iodo]benzene; lithium hexamethyldisilazane; In tetrahydrofuran; methanol; tetrachloromethane; ethanol; dichloromethane; water; toluene;
DOI:10.1002/anie.202104410