(Δ^2,3E,Δ^6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol

Base Information

• Chemical Name: (Δ^2,3E,Δ^6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol
• CAS No.: 145014-09-1
• Molecular Formula: C₂₆H₃₅BrOSi
• Molecular Weight: 471.553

Synonyms:(Δ^2,3E,Δ^6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol

Chemical Property of (Δ^2,3E,Δ^6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol

Chemical Property:

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Technology Process of (Δ^2,3E,Δ^6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol

There total 5 articles about (Δ^2,3E,Δ^6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol 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:

Methanesulfonic acid (2E,6E)-8-(tert-butyl-diphenyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienyl ester (412347-67-2) → (Δ2,3E,Δ6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol (145014-09-1)

Guidance literature:

With lithium bromide; In tetrahydrofuran; at 0 ℃; for 1h; Yield given;

DOI:10.1016/S0040-4039(00)79008-3

Reference yield:

(Δ2,3E,Δ6,7E)-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1,8-diol (117638-13-8) → (Δ2,3E,Δ6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol (145014-09-1)

Guidance literature:

Multi-step reaction with 2 steps

1: Et₃N / CH₂Cl₂ / 1 h / -40 °C

2: 1.34 g / LiBr / tetrahydrofuran / 1 h / 0 °C

With triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ol048212e

Reference yield:

Geraniol (106-24-1) → (Δ2,3E,Δ6,7E)-8-bromo-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1-ol (145014-09-1)

Guidance literature:

Multi-step reaction with 4 steps

1: imidazole / CH₂Cl₂ / 1 h / 0 °C

2: 1.34 g / t-BuOOH; SeO₂ / H₂O; CH₂Cl₂ / 48 h / 0 °C

3: Et₃N / CH₂Cl₂ / 1 h / -40 °C

4: 1.34 g / LiBr / tetrahydrofuran / 1 h / 0 °C

With 1H-imidazole; tert.-butylhydroperoxide; selenium(IV) oxide; triethylamine; lithium bromide; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol048212e

upstream raw materials:

Methanesulfonic acid (2E,6E)-8-(tert-butyl-diphenyl-silanyloxy)-2,6-dimethyl-octa-2,6-dienyl ester

Geraniol

tert-butyl ({[(2E)-3,7-dimethylocta-2,6-dien-1-yl]oxy})diphenylsilane

(Δ^2,3E,Δ^6,7E)-1-O-tert-butyldiphenylsilyl-3,7-dimethyl-octa-2,6-dien-1,8-diol

Downstream raw materials:

(2E,6E,10E)-1-tert-butyldiphenylsiloxy-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

tert-Butyl-((2E,6E,10E,14E)-3,7,11,15,19-pentamethyl-icosa-2,6,10,14,18-pentaenyloxy)-diphenyl-silane

geranylfarnesol

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