(1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde

Base Information

• Chemical Name: (1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde
• CAS No.: 159249-16-8
• Molecular Formula: C₂₇H₃₈O₂Si
• Molecular Weight: 422.683
• Mol file: 159249-16-8.mol

Synonyms:(1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde

Chemical Property of (1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde

There total 12 articles about (1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde 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: 92.0%

(1S,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde → (1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde (159249-16-8)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; for 5h; Heating;

DOI:10.1021/ja00095a078

Reference yield:

(±)-(1R*,4R*)-4-methylcyclohex-2-enol (21592-97-2,23713-60-2,23713-61-3) → (1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde (159249-16-8)

Guidance literature:

Multi-step reaction with 12 steps

2: 1.) 2,4-dinitrophenol, 2.) KOH / 1.) reflux, 3 d, 2.) MeOH, reflux, 20 h

3: 1.) NBS, 2.) DBU / 1.) CH₂Cl₂, 25 deg C, 12 h, 2.) xylene, reflux, 2 h

4: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 0.5 h

5: 1.) LDA, 2.) H₂O / 1.) THF, -78 deg C, 1 h

6: H₂ / 5percent Pd/C / diethyl ether / 4 h / 25 °C / 1292.9 Torr

7: LAH / tetrahydrofuran / 1 h / -78 - 25 °C

8: 98 percent / DMAP, TEA / CH₂Cl₂ / 2 h / 0 °C

9: 89 percent / PDC / CH₂Cl₂ / 10 h / 25 °C

10: 1.) n-BuLi / 2.) THF, 25 deg C, 2 h

11: 95 percent / TCA, H₂O / CH₂Cl₂ / 0.5 h / 25 °C

12: 92 percent / DBU / methanol / 5 h / Heating

With dmap; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 2,4-Dinitrophenol; TEA; water; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; trichloroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00095a078

Reference yield:

(1S,4S)-(-)-Methyl-2-cyclohexen-1-ol (159249-15-7) → (1R,2R,3S)-2-[(R)-2-(tert-Butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-3-methyl-cyclohexanecarbaldehyde (159249-16-8)

Guidance literature:

Multi-step reaction with 11 steps

1: 1.) 2,4-dinitrophenol, 2.) KOH / 1.) reflux, 3 d, 2.) MeOH, reflux, 20 h

2: 1.) NBS, 2.) DBU / 1.) CH₂Cl₂, 25 deg C, 12 h, 2.) xylene, reflux, 2 h

3: 1.) LDA / 1.) THF, -78 deg C, 1 h, 2.) THF, -78 deg C, 0.5 h

4: 1.) LDA, 2.) H₂O / 1.) THF, -78 deg C, 1 h

5: H₂ / 5percent Pd/C / diethyl ether / 4 h / 25 °C / 1292.9 Torr

6: LAH / tetrahydrofuran / 1 h / -78 - 25 °C

7: 98 percent / DMAP, TEA / CH₂Cl₂ / 2 h / 0 °C

8: 89 percent / PDC / CH₂Cl₂ / 10 h / 25 °C

9: 1.) n-BuLi / 2.) THF, 25 deg C, 2 h

10: 95 percent / TCA, H₂O / CH₂Cl₂ / 0.5 h / 25 °C

11: 92 percent / DBU / methanol / 5 h / Heating

With dmap; potassium hydroxide; N-Bromosuccinimide; lithium aluminium tetrahydride; dipyridinium dichromate; n-butyllithium; 2,4-Dinitrophenol; TEA; water; hydrogen; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium diisopropyl amide; trichloroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1021/ja00095a078

upstream raw materials:

(1S,4S)-(-)-Methyl-2-cyclohexen-1-ol

(±)-(1R*,4R*)-4-methylcyclohex-2-enol

(3aR,4S,7aS)-4-Methyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one

((1R,6S)-6-Methyl-cyclohex-2-enyl)-acetic acid