(1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde

Base Information

• Chemical Name: (1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde
• CAS No.: 342375-07-9
• Molecular Formula: C₃₀H₄₀O₂Si
• Molecular Weight: 460.732

Synonyms:

Chemical Property of (1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde

There total 16 articles about (1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde 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%

[(1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl]-methanol (342375-15-9) → (1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde (342375-07-9)

Guidance literature:

In dichloromethane;

DOI:10.1016/S0040-4039(01)00217-9

Reference yield:

(R)-Citronellal (2385-77-5) → (1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde (342375-07-9)

Guidance literature:

Multi-step reaction with 15 steps

2: 86 percent / chromous chloride; LiI / tetrahydrofuran

3: 87 percent / Ph₃P; NaOH / Pd₂((dba)2*CHCl₃ / tetrahydrofuran; H₂O / Heating

4: 99 percent / DIBAL-H / tetrahydrofuran / -78 °C

5: 94 percent / i-Pr₂NEt; 4-DMAP / CH₂Cl₂

6: 98 percent / n-Bu₄NF / tetrahydrofuran

7: 91 percent / CH₂Cl₂ / -78 °C

8: 99 percent / benzene / Heating

9: 94 percent / DIBAL-H / tetrahydrofuran / -78 °C

10: 93 percent / CH₂Cl₂ / -78 °C

11: 75 percent / Me₃Al / CH₂Cl₂ / 4 h / 0 °C

12: NaBH₄ / ethanol / 0 °C

13: 92 percent / imidazole; 4-DMAP / CH₂Cl₂

14: 62 percent / bromotrimethylsilane / CH₂Cl₂

15: 95 percent / CH₂Cl₂

With 1H-imidazole; chromium dichloride; dmap; sodium hydroxide; sodium tetrahydroborate; trimethylsilyl bromide; tetrabutyl ammonium fluoride; trimethylaluminum; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; ethanol; dichloromethane; water; benzene; 3: Suzuki coupling / 7: Swern oxidation / 8: Wittig reaction / 10: Swern oxidation / 11: intramolecular Diels-Alder reaction / 15: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(01)00217-9

Reference yield:

(R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hexanal (342374-96-3) → (1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalene-2-carbaldehyde (342375-07-9)

Guidance literature:

Multi-step reaction with 14 steps

1: 86 percent / chromous chloride; LiI / tetrahydrofuran

2: 87 percent / Ph₃P; NaOH / Pd₂((dba)2*CHCl₃ / tetrahydrofuran; H₂O / Heating

3: 99 percent / DIBAL-H / tetrahydrofuran / -78 °C

4: 94 percent / i-Pr₂NEt; 4-DMAP / CH₂Cl₂

5: 98 percent / n-Bu₄NF / tetrahydrofuran

6: 91 percent / CH₂Cl₂ / -78 °C

7: 99 percent / benzene / Heating

8: 94 percent / DIBAL-H / tetrahydrofuran / -78 °C

9: 93 percent / CH₂Cl₂ / -78 °C

10: 75 percent / Me₃Al / CH₂Cl₂ / 4 h / 0 °C

11: NaBH₄ / ethanol / 0 °C

12: 92 percent / imidazole; 4-DMAP / CH₂Cl₂

13: 62 percent / bromotrimethylsilane / CH₂Cl₂

14: 95 percent / CH₂Cl₂

With 1H-imidazole; chromium dichloride; dmap; sodium hydroxide; sodium tetrahydroborate; trimethylsilyl bromide; tetrabutyl ammonium fluoride; trimethylaluminum; diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium iodide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; In tetrahydrofuran; ethanol; dichloromethane; water; benzene; 2: Suzuki coupling / 6: Swern oxidation / 7: Wittig reaction / 9: Swern oxidation / 10: intramolecular Diels-Alder reaction / 14: Dess-Martin oxidation;

DOI:10.1016/S0040-4039(01)00217-9

upstream raw materials:

[(1S,2R,4aS,6R,8aR)-1-(tert-Butyl-diphenyl-silanyloxymethyl)-1,6-dimethyl-1,2,4a,5,6,7,8,8a-octahydro-naphthalen-2-yl]-methanol

(R)-Citronellal

tert-butylchlorodiphenylsilane

(R)-6-(tert-Butyl-diphenyl-silanyloxy)-3-methyl-hexanal

Downstream raw materials:

(-)-equisetin

5'-epiequisetin

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