2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol

Base Information

• Chemical Name: 2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol
• CAS No.: 214629-61-5
• Molecular Formula: C₁₉H₃₀O₂Si
• Molecular Weight: 318.531

Synonyms:2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol

Chemical Property of 2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol

Chemical Property:

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Technology Process of 2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol

There total 3 articles about 2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol 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: 78.0%

tert-Butyl-dimethyl-((1R,4S,4aR,5S,8S,8aS)-8-m-tolyloxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yloxy)-silane (214629-56-8) → 2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol (214629-61-5)

Guidance literature:

In diphenylether; for 0.5h; Heating;

DOI:10.1055/s-1998-1844

Reference yield:

(-)-(1S,4R,4aS,5R,8S,8aR)-8-tert-Butyldimethylsilyloxy-1,4,4a,5,6,8,8a-octahydro-5-hydroxy-endo-1,4-methanonaphthalene (214629-54-6) → 2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol (214629-61-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / diisopropyl azodicarboxylate, PPh₃ / tetrahydrofuran

2: diphenyl ether / 0.08 h / Heating

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; diphenylether;

DOI:10.1055/s-1998-1844

Reference yield:

tert-Butyl-dimethyl-((1R,4S,4aR,5S,8S,8aS)-8-m-tolyloxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yloxy)-silane (214629-56-8) → tert-Butyl-dimethyl-((1S,4S)-4-m-tolyloxy-cyclohex-2-enyloxy)-silane + 2-[(1R,6S)-6-(tert-Butyl-dimethyl-silanyloxy)-cyclohex-2-enyl]-5-methyl-phenol (214629-61-5)

Guidance literature:

In diphenylether; for 0.0833333h; Heating;

DOI:10.1055/s-1998-1844

upstream raw materials:

tert-Butyl-dimethyl-((1R,4S,4aR,5S,8S,8aS)-8-m-tolyloxy-1,4,4a,5,6,7,8,8a-octahydro-1,4-methano-naphthalen-5-yloxy)-silane

(-)-(1S,4R,4aS,5R,8S,8aR)-8-tert-Butyldimethylsilyloxy-1,4,4a,5,6,8,8a-octahydro-5-hydroxy-endo-1,4-methanonaphthalene

Downstream raw materials:

(S)-2-(6-hydroxy-6-methylheptan-2-yl)-5-methylphenol

(S)-5-(2-Hydroxy-4-methyl-phenyl)-hexanoic acid methyl ester

2,2-Dimethyl-propionic acid (4S,5R)-4-(tert-butyl-dimethyl-silanyloxy)-5-(2-methoxy-4-methyl-phenyl)-hexyl ester

2,2-Dimethyl-propionic acid (4S,5S)-4-(tert-butyl-dimethyl-silanyloxy)-6-hydroxy-5-(2-methoxy-4-methyl-phenyl)-hexyl ester

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