(1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.0^2,7]tridec-5-en-9-one

Base Information

• Chemical Name: (1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.0^2,7]tridec-5-en-9-one
• CAS No.: 287934-84-3
• Molecular Formula: C₃₀H₃₆O₄Si
• Molecular Weight: 488.699
• Mol file: 287934-84-3.mol

Synonyms:(1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.0^2,7]tridec-5-en-9-one

Chemical Property of (1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.0^2,7]tridec-5-en-9-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.0^2,7]tridec-5-en-9-one

There total 13 articles about (1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.0^2,7]tridec-5-en-9-one 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) → (1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.02,7]tridec-5-en-9-one (287934-84-3)

Guidance literature:

Multi-step reaction with 9 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

With dmap; lithium hydroxide; cerium(III) chloride; boron trifluoride diethyl etherate; oxonium; tetrabutylammomium bromide; oxygen; diisobutylaluminium hydride; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Wacker oxidation / 9: Yonemitsu/Yamaguchi protocol;

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) → (1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.02,7]tridec-5-en-9-one (287934-84-3)

Guidance literature:

Multi-step reaction with 8 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

With dmap; lithium hydroxide; cerium(III) chloride; boron trifluoride diethyl etherate; oxonium; oxygen; diisobutylaluminium hydride; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 4: Wacker oxidation / 8: Yonemitsu/Yamaguchi protocol;

DOI:10.1021/ja011285y

Reference yield:

Acetic acid (3R,3aS,5R,7aR)-3-allyl-5-(tert-butyl-diphenyl-silanyloxy)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-yl ester → (1R,2S,4R,7R,8R,11R)-4-(tert-Butyl-diphenyl-silanyloxy)-11-methyl-11-vinyl-10,13-dioxa-tricyclo[6.4.1.02,7]tridec-5-en-9-one (287934-84-3)

Guidance literature:

Multi-step reaction with 6 steps

1: BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

2: 86 percent / O₂; PdCl₂; aq. CuCl / dimethylformamide

3: 87 percent / CeCl₃ / tetrahydrofuran

4: 91 percent / H₃O⁺ / methanol

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

6: Cl₃C₆H₂COCl; Et₃N; DMAP / toluene

With dmap; lithium hydroxide; cerium(III) chloride; boron trifluoride diethyl etherate; oxonium; oxygen; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 2: Wacker oxidation / 6: Yonemitsu/Yamaguchi protocol;

DOI:10.1021/ja011285y

upstream raw materials:

(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-hydroxy-2-methyl-but-3-enyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carboxylic acid

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

(3S,3aS,7aR)-3-((1S,2R,5S)-2-Isopropyl-5-methyl-cyclohexyloxy)-3a,7a-dihydro-3H,4H-isobenzofuran-1,5-dione

Downstream raw materials:

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

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

(Z)-(1R,2S,4R,7R,8R,9R)-4-(tert-Butyl-diphenyl-silanyloxy)-9,13-dimethyl-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-ol

(Z)-(1R,2S,4R,7R,8R)-4-(tert-Butyl-diphenyl-silanyloxy)-13-methyl-15-oxa-tricyclo[6.6.1.0^2,7]pentadeca-5,12-dien-9-one