Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester

Base Information

• Chemical Name: Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester
• CAS No.: 287934-72-9
• Molecular Formula: C₂₃H₂₆O₄
• Molecular Weight: 366.457

Synonyms:Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester

Chemical Property of Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester

There total 18 articles about Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester 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:

5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one (198191-73-0) → Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.02,7]pentadeca-5,12-dien-9-yl ester (287934-72-9)

Guidance literature:

Multi-step reaction with 15 steps

1: aq. Bu₄NBr / tetrahydrofuran

2: Dibal-H / CH₂Cl₂ / -78 °C

3: Et₃N / CH₂Cl₂ / -78 - 20 °C

4: BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

5: 86 percent / O₂; PdCl₂; aq. CuCl / dimethylformamide

6: 87 percent / CeCl₃ / tetrahydrofuran

7: 91 percent / H₃O⁺ / methanol

8: aq. LiOH / tetrahydrofuran; methanol / -30 - 0 °C

9: Cl₃C₆H₂COCl; Et₃N; DMAP / toluene

10: 61 percent / py / tetrahydrofuran / -50 - 20 °C

11: 76 percent / p-cymene / 1.5 h / 140 °C

12: 88 percent / NaBF₄ / tetrahydrofuran

13: 91 percent / KH / tetrahydrofuran

14: TBAF / tetrahydrofuran

15: TPAP; NMO; 4A MS / CH₂Cl₂

With pyridine; dmap; lithium hydroxide; sodium tetrafluoroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4-methylisopropylbenzene; boron trifluoride diethyl etherate; oxonium; tetrabutyl ammonium fluoride; tetrabutylammomium bromide; oxygen; potassium hydride; diisobutylaluminium hydride; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Wacker oxidation / 9: Yonemitsu/Yamaguchi protocol / 11: Claisen rearrangement;

DOI:10.1021/ja011285y

Reference yield:

(3R,3aS,5R,7aR)-3-Allyl-5-(tert-butyl-diphenyl-silanyloxy)-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one (198191-76-3) → Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.02,7]pentadeca-5,12-dien-9-yl ester (287934-72-9)

Guidance literature:

Multi-step reaction with 14 steps

1: Dibal-H / CH₂Cl₂ / -78 °C

2: Et₃N / CH₂Cl₂ / -78 - 20 °C

3: BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

4: 86 percent / O₂; PdCl₂; aq. CuCl / dimethylformamide

5: 87 percent / CeCl₃ / tetrahydrofuran

6: 91 percent / H₃O⁺ / methanol

7: aq. LiOH / tetrahydrofuran; methanol / -30 - 0 °C

8: Cl₃C₆H₂COCl; Et₃N; DMAP / toluene

9: 61 percent / py / tetrahydrofuran / -50 - 20 °C

10: 76 percent / p-cymene / 1.5 h / 140 °C

11: 88 percent / NaBF₄ / tetrahydrofuran

12: 91 percent / KH / tetrahydrofuran

13: TBAF / tetrahydrofuran

14: TPAP; NMO; 4A MS / CH₂Cl₂

With pyridine; dmap; lithium hydroxide; sodium tetrafluoroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4-methylisopropylbenzene; boron trifluoride diethyl etherate; oxonium; tetrabutyl ammonium fluoride; oxygen; potassium hydride; diisobutylaluminium hydride; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Wacker oxidation / 8: Yonemitsu/Yamaguchi protocol / 10: Claisen rearrangement;

DOI:10.1021/ja011285y

Reference yield:

(3R,3aS,5R,7aR)-3-Allyl-5-(tert-butyl-diphenyl-silanyloxy)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-ol (369362-22-1) → Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.02,7]pentadeca-5,12-dien-9-yl ester (287934-72-9)

Guidance literature:

Multi-step reaction with 13 steps

1: Et₃N / CH₂Cl₂ / -78 - 20 °C

2: BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

3: 86 percent / O₂; PdCl₂; aq. CuCl / dimethylformamide

4: 87 percent / CeCl₃ / tetrahydrofuran

5: 91 percent / H₃O⁺ / methanol

6: aq. LiOH / tetrahydrofuran; methanol / -30 - 0 °C

7: Cl₃C₆H₂COCl; Et₃N; DMAP / toluene

8: 61 percent / py / tetrahydrofuran / -50 - 20 °C

9: 76 percent / p-cymene / 1.5 h / 140 °C

10: 88 percent / NaBF₄ / tetrahydrofuran

11: 91 percent / KH / tetrahydrofuran

12: TBAF / tetrahydrofuran

13: TPAP; NMO; 4A MS / CH₂Cl₂

With pyridine; dmap; lithium hydroxide; sodium tetrafluoroborate; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; 4-methylisopropylbenzene; boron trifluoride diethyl etherate; oxonium; tetrabutyl ammonium fluoride; oxygen; potassium hydride; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 3: Wacker oxidation / 7: Yonemitsu/Yamaguchi protocol / 9: Claisen rearrangement;

DOI:10.1021/ja011285y

upstream raw materials:

Benzoic acid (Z)-(1R,2S,4R,7R,8R,9R)-4-hydroxy-9,13-dimethyl-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester

5-(tert-butyl-diphenyl-silanyloxy)-3-hydroxy-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one

(3R,3aS,5R,7aR)-3-Allyl-5-(tert-butyl-diphenyl-silanyloxy)-3a,4,5,7a-tetrahydro-3H-isobenzofuran-1-one

(3R,3aS,5R,7aR)-3-Allyl-5-(tert-butyl-diphenyl-silanyloxy)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-ol

Downstream raw materials:

Benzoic acid (Z)-(1R,2R,3S,7R,8R,9R)-9,13-dimethyl-4-oxo-3-phenylsulfanylmethyl-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester

Benzoic acid (Z)-(1R,2R,7R,8R,9R)-9,13-dimethyl-4-trimethylsilanyloxy-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-3,5,12-trien-9-yl ester

Post a RFQ

Cas No.:

Product Name:

Quantity:

Please select Metric Ton KG G Pound L ML

Email:

Company name:

Valid Period:

Detailed Requirements:

• Sample
• MOQ
• GMP
• FDA
• Price
  FOB CIF CFR EXW
• Urgent purchase

Enter 15 to 2000 letters.Word count: 0 letters

Attach files(File Format: Jpeg, Jpg, Gif, Png, PDF, PPT, Zip, Rar,Word or Excel Maximum File Size: 3MB)

Remove

Submit

1

What can I do for you?
Get Best Price

Get Best Price for 287934-72-9 Benzoic acid (Z)-(1R,2S,7R,8R,9R)-9,13-dimethyl-4-oxo-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-yl ester

Send

Send

Metric Ton KG G Pound L ML

Send

Send