tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane
• CAS No.: 909193-79-9
• Molecular Formula: C₂₀H₃₈OSi
• Molecular Weight: 322.607

Synonyms:tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane

Chemical Property of tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane

Chemical Property:

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Technology Process of tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane

There total 4 articles about tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane 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: 95.0%

(3R,4S)(E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-ol (909193-78-8) + t-butyldimethylsiyl triflate (69739-34-0) → tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane (909193-79-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at -20 - 20 ℃; for 1.5h;

DOI:10.1021/ol0612612

Reference yield:

(S)(Z)-{1-[(2-methylallyl)oxy]but-2-en-1-yl}cyclohexane (909193-77-7) → tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane (909193-79-9)

Guidance literature:

Multi-step reaction with 2 steps

1: potassium tert-butoxide; n-butyllithium / tetrahydrofuran / 14 h / -20 - 0 °C

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -20 - 20 °C

With 2,6-dimethylpyridine; n-butyllithium; potassium tert-butylate; In tetrahydrofuran; dichloromethane; 1: 2,3-Wittig rearragement;

DOI:10.1021/ol0612612

Reference yield:

(Z,S)-α-(1-Propenyl)cyclohexanemethanol (130930-52-8) → tert-Butyl-((E)-(1R,2S)-4-cyclohexyl-1-isopropenyl-2-methyl-but-3-enyloxy)-dimethyl-silane (909193-79-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 85 percent / sodium hydride / tetrahydrofuran / Heating

2: potassium tert-butoxide; n-butyllithium / tetrahydrofuran / 14 h / -20 - 0 °C

3: 95 percent / 2,6-lutidine / CH₂Cl₂ / 1.5 h / -20 - 20 °C

With 2,6-dimethylpyridine; n-butyllithium; potassium tert-butylate; sodium hydride; In tetrahydrofuran; dichloromethane; 2: 2,3-Wittig rearragement;

DOI:10.1021/ol0612612

upstream raw materials:

(3R,4S)(E)-6-cyclohexyl-2,4-dimethylhexa-1,5-dien-3-ol

t-butyldimethylsiyl triflate

(S)(Z)-{1-[(2-methylallyl)oxy]but-2-en-1-yl}cyclohexane

(Z,S)-α-(1-Propenyl)cyclohexanemethanol

Downstream raw materials:

(E)-(2S,3R,4S)-3-(tert-Butyl-dimethyl-silanyloxy)-6-cyclohexyl-2,4-dimethyl-hex-5-en-1-ol

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