(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-carbonitrile

Base Information

• Chemical Name: (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-carbonitrile
• CAS No.: 287934-67-2
• Molecular Formula: C₃₀H₃₇NO₃Si
• Molecular Weight: 487.714
• Mol file: 287934-67-2.mol

Synonyms:(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-carbonitrile

Chemical Property of (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-carbonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (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-carbonitrile

There total 11 articles about (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-carbonitrile 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: 87.0%

vinyl magnesium bromide (1826-67-1) + (1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-oxo-propyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carbonitrile (287934-66-1) → (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-carbonitrile (287934-67-2)

Guidance literature:

With cerium(III) chloride; In tetrahydrofuran;

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,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-carbonitrile (287934-67-2)

Guidance literature:

Multi-step reaction with 3 steps

1: BF₃*OEt₂ / CH₂Cl₂ / -78 - 20 °C

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

3: 87 percent / CeCl₃ / tetrahydrofuran

With cerium(III) chloride; boron trifluoride diethyl etherate; oxygen; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 2: Wacker oxidation;

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) → (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-carbonitrile (287934-67-2)

Guidance literature:

Multi-step reaction with 4 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

With cerium(III) chloride; boron trifluoride diethyl etherate; oxygen; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Wacker oxidation;

DOI:10.1021/ja011285y

upstream raw materials:

vinyl magnesium bromide

(1R,3R,3aS,5R,7aR)-5-(tert-Butyl-diphenyl-silanyloxy)-3-(2-oxo-propyl)-1,3,3a,4,5,7a-hexahydro-isobenzofuran-1-carbonitrile

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

Downstream 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

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

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

(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