(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one

Base Information

• Chemical Name: (1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one
• CAS No.: 945553-45-7
• Molecular Formula: C₂₉H₄₆O₇Si
• Molecular Weight: 534.766
• Mol file: 945553-45-7.mol

Synonyms:(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one

Chemical Property of (1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one

There total 1 articles about (1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-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:

catechinic acid (945553-39-9) + triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + dimethyl sulfate (77-78-1) + trimethyl orthoformate (149-73-5) → (1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one (945553-45-7) + (1R,5R,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-4,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-3-en-2-one (945553-46-8)

Guidance literature:

catechinic acid; dimethyl sulfate; With potassium carbonate; In acetone; for 18h; Heating;

trimethyl orthoformate; With toluene-4-sulfonic acid; In methanol; for 24h; Heating;

triisopropylsilyl trifluoromethanesulfonate; With 2,6-dimethylpyridine; In dichloromethane; at 20 - 25 ℃; Further stages.;

DOI:10.1039/b704311b

Reference yield: 75.0%

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one (945553-45-7) + prenyl bromide (870-63-3) → (1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-5-(prenyl)-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one (945553-47-9)

Guidance literature:

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

prenyl bromide; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Further stages.;

DOI:10.1039/b704311b

Reference yield: 67.0%

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one (945553-45-7) + diphenyldisulfane (882-33-7) → (1S,5R,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-5-phenylsulfanyl-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one

Guidance literature:

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 3h;

diphenyldisulfane; In tetrahydrofuran; hexane; at -78 ℃; for 3h; Further stages.;

DOI:10.1039/b704311b

upstream raw materials:

catechinic acid

triisopropylsilyl trifluoromethanesulfonate

dimethyl sulfate

trimethyl orthoformate

Downstream raw materials:

(1S,5S,7S,8R)-(+)-8-(3,4-dimethoxyphenyl)-2,9,9-trimethoxy-5-(prenyl)-7-triisopropylsilanyloxy-bicyclo[3.3.1]non-2-en-4-one