11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene

Base Information

• Chemical Name: 11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene
• CAS No.: 257288-31-6
• Molecular Formula: C₄₁H₅₆O₃Si
• Molecular Weight: 624.979
• Mol file: 257288-31-6.mol

Synonyms:11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene

Chemical Property of 11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene

There total 4 articles about 11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene 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: 79.0%

(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1-carboxaldehyde (68985-10-4) + 3,4-di-O-benzyl-2-bromo-1-O-tert-butyldimethylsilylbenzenetriol (189082-99-3) → 11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene (257288-31-6)

Guidance literature:

(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1-carboxaldehyde; 3,4-di-O-benzyl-2-bromo-1-O-tert-butyldimethylsilylbenzenetriol; With tert.-butyl lithium; In diethyl ether; pentane; at -78 ℃; for 1.5h;

With triethylsilane; trifluoroacetic acid; In dichloromethane; at -78 ℃; for 0.75h;

DOI:10.1016/S0040-4020(99)00992-8

Reference yield:

3,4-dibenzyloxyphenol (27688-86-4) → 11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene (257288-31-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / imidazole / dimethylformamide / 15 h / 20 °C

2.1: 97 percent / N-bromosuccinimide; silica gel / CCl₄ / 0.25 h / 20 °C

3.1: t-BuLi / pentane; diethyl ether / 1.5 h / -78 °C

3.2: 79 percent / Et₃SiH; TFA / CH₂Cl₂ / 0.75 h / -78 °C

With 1H-imidazole; N-Bromosuccinimide; tert.-butyl lithium; silica gel; In tetrachloromethane; diethyl ether; N,N-dimethyl-formamide; pentane; 1.1: silylation / 2.1: Bromination / 3.1: Condensation / 3.2: cationic reduction;

DOI:10.1016/S0040-4020(99)00992-8

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → 11-(2-tert-butyldimethylsilyloxy-4,5-di-benzyloxyphenyl)-8-drimene (257288-31-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 92 percent / imidazole / dimethylformamide / 15 h / 20 °C

2.1: 97 percent / N-bromosuccinimide; silica gel / CCl₄ / 0.25 h / 20 °C

3.1: t-BuLi / pentane; diethyl ether / 1.5 h / -78 °C

3.2: 79 percent / Et₃SiH; TFA / CH₂Cl₂ / 0.75 h / -78 °C

With 1H-imidazole; N-Bromosuccinimide; tert.-butyl lithium; silica gel; In tetrachloromethane; diethyl ether; N,N-dimethyl-formamide; pentane; 1.1: silylation / 2.1: Bromination / 3.1: Condensation / 3.2: cationic reduction;

DOI:10.1016/S0040-4020(99)00992-8

upstream raw materials:

(4aS,8aS)-3,4,4a,5,6,7,8,8a-octahydro-2,5,5,8a-tetramethylnaphthalene-1-carboxaldehyde

3,4-di-O-benzyl-2-bromo-1-O-tert-butyldimethylsilylbenzenetriol

3,4-dibenzyloxyphenol

tert-butyldimethylsilyl chloride

Downstream raw materials:

acetate of 2-(8α,9α-epoxy-driman-11-yl)-4,5-dibenzyloxyphenyl

acetate of 2-(8β,9β-epoxy-driman-11-yl)-4,5-dibenzyloxyphenyl

9α-hydroxy-di-O-benzylpuupehenol

acetate of 2-(8-drimen-11-yl)-4,5-dibenzyloxyphenyl