(1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Base Information

• Chemical Name: (1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde
• CAS No.: 816455-40-0
• Molecular Formula: C₄₀H₄₉BrO₃Si
• Molecular Weight: 685.817
• Mol file: 816455-40-0.mol

Synonyms:(1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Chemical Property of (1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

There total 12 articles about (1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde 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: 96.0%

(1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde (816455-37-5) + tert-butylchlorodiphenylsilane (58479-61-1) → (1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde (816455-40-0)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; at 20 ℃; for 1h;

DOI:10.1002/chem.200400444

Reference yield:

(1R,2S,3S,4S)-2-exo-methyl-3-endo-phenylnorbornene-2-carbaldehyde (816454-32-7,816454-13-4,816454-36-1) → (1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde (816455-40-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / p-TsOH / toluene / 24 h / 20 °C

2: NBS / -40 - 20 °C

3: 66.8 mg / aq. p-TsOH / acetone / 20 °C

4: 96 percent / imidazole / dimethylformamide / 1 h / 20 °C

With 1H-imidazole; N-Bromosuccinimide; toluene-4-sulfonic acid; In N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1002/chem.200400444

Reference yield:

2-exo-methyl-3-endo-phenylnorbornene-2-carbaldehyde (816454-13-4,816454-36-1) → (1S,2R,3S,4R,5R,6R)-6-[(1S,3R)-1-Allyl-3-(tert-butyl-diphenyl-silanyloxy)-hex-5-enyloxy]-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde (816455-40-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: p-TsOH / toluene / 3 h / 20 °C

1.2: 36 percent / aq. NBS / acetonitrile / 20 h / 20 °C

2.1: Zn(OTf)2 / N,N-dimethyl-acetamide / 0.5 h / 40 °C

2.2: 85 percent / Zn / N,N-dimethyl-acetamide / 5 h / 70 °C

3.1: 90 percent / p-TsOH / toluene / 24 h / 20 °C

4.1: NBS / -40 - 20 °C

5.1: 66.8 mg / aq. p-TsOH / acetone / 20 °C

6.1: 96 percent / imidazole / dimethylformamide / 1 h / 20 °C

With 1H-imidazole; N-Bromosuccinimide; zinc trifluoromethanesulfonate; toluene-4-sulfonic acid; In N,N-dimethyl acetamide; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1002/chem.200400444

upstream raw materials:

(1S,2R,3S,4R,5R,6R)-6-((1S,3R)-1-Allyl-3-hydroxy-hex-5-enyloxy)-5-bromo-2-methyl-3-phenyl-bicyclo[2.2.1]heptane-2-carbaldehyde

tert-butylchlorodiphenylsilane

(1R,2S,3S,4S)-2-exo-methyl-3-endo-phenylnorbornene-2-carbaldehyde

2-exo-methyl-3-endo-phenylnorbornene-2-carbaldehyde