1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene

Base Information

• Chemical Name: 1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene
• CAS No.: 121314-05-4
• Molecular Formula: C₂₉H₅₀O₄Si₂
• Molecular Weight: 518.885
• Mol file: 121314-05-4.mol

Synonyms:

Chemical Property of 1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene

There total 11 articles about 1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene 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:

(1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol (35692-59-2) → 1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene (121314-05-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 98 percent / imidazole / dimethylformamide

3: 96 percent / diethylaluminium 2,2,6,6-tetramethylpiperidide (DATMP) / benzene / 0 °C

4: DMAP / CH₂Cl₂

5: NaI / acetone / Heating

6: 97 percent / CrCl₃, LAH / tetrahydrofuran

7: diethyl azodicarboxylate (DEAD), triphenylphosphine / tetrahydrofuran / Ambient temperature

With 1H-imidazole; dmap; chromium chloride; lithium aluminium tetrahydride; diethyl(2,2,6,6-tetramethylpiperidino)aluminium; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00276a003

Reference yield:

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one (36616-60-1) → 1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene (121314-05-4)

Guidance literature:

Multi-step reaction with 8 steps

1: L-Selectride / tetrahydrofuran / -65 °C

2: 98 percent / imidazole / dimethylformamide

4: 96 percent / diethylaluminium 2,2,6,6-tetramethylpiperidide (DATMP) / benzene / 0 °C

5: DMAP / CH₂Cl₂

6: NaI / acetone / Heating

7: 97 percent / CrCl₃, LAH / tetrahydrofuran

8: diethyl azodicarboxylate (DEAD), triphenylphosphine / tetrahydrofuran / Ambient temperature

With 1H-imidazole; dmap; chromium chloride; lithium aluminium tetrahydride; diethyl(2,2,6,6-tetramethylpiperidino)aluminium; L-Selectride; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00276a003

Reference yield:

(R)-Carvone (6485-40-1,2244-16-8) → 1-{(Z)-2-[(1R,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-vinyloxymethyl}-4-methoxy-benzene (121314-05-4)

Guidance literature:

Multi-step reaction with 9 steps

1: 90 percent / H₂O₂, NaOH / methanol

2: L-Selectride / tetrahydrofuran / -65 °C

3: 98 percent / imidazole / dimethylformamide

5: 96 percent / diethylaluminium 2,2,6,6-tetramethylpiperidide (DATMP) / benzene / 0 °C

6: DMAP / CH₂Cl₂

7: NaI / acetone / Heating

8: 97 percent / CrCl₃, LAH / tetrahydrofuran

9: diethyl azodicarboxylate (DEAD), triphenylphosphine / tetrahydrofuran / Ambient temperature

With 1H-imidazole; dmap; chromium chloride; sodium hydroxide; lithium aluminium tetrahydride; diethyl(2,2,6,6-tetramethylpiperidino)aluminium; dihydrogen peroxide; L-Selectride; triphenylphosphine; sodium iodide; diethylazodicarboxylate; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; benzene;

DOI:10.1021/jo00276a003

upstream raw materials:

(S)-1-[(1S,3S,5R)-3,5-Bis-(tert-butyl-dimethyl-silanyloxy)-2-methylene-cyclohexyl]-2-(4-methoxy-benzyloxy)-ethanol

(1S,2S,4S,6R)-1-methyl-4-(prop-1-en-2-yl)-7-oxabicyclo[4.1.0]heptan-2-ol

(1R,4R,6R)-4-isopropenyl-1-methyl-7-oxabicyclo[4.1.0]heptan-2-one

(R)-Carvone