(2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal

Base Information

• Chemical Name: (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal
• CAS No.: 138490-51-4
• Molecular Formula: C₁₀H₁₈O₂
• Molecular Weight: 170.252
• Mol file: 138490-51-4.mol

Synonyms:

Chemical Property of (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal

There total 10 articles about (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal 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:

propionaldehyde (123-38-6) + cyclohexanecarbaldehyde (2043-61-0) → (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal (138490-51-4)

Guidance literature:

With 3-butyl-1-methyl-1H-imidazol-3-ium hexafluorophosphate; D-Prolin; In N,N-dimethyl-formamide; at 4 ℃;

DOI:10.1016/j.tetlet.2004.03.080

Reference yield:

(1R*,2S*)-1-cyclohexyl-2-methyl-1,3-bis(trimethylsiloxy)propane (135067-18-4) → (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal (138490-51-4)

Guidance literature:

Multi-step reaction with 3 steps

1: trimethylsilyl trifluoromethanesulfonate (TMSOTf) / CH₂Cl₂ / 18 h / -40 °C

2: 85 percent / p-toluenesulfonic acid / methanol / Ambient temperature

3: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -85 deg C, 20 min, 2.a) -85 deg C, 30 min, b) -85 deg C to r.t., 50 min

With oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; dichloromethane;

DOI:10.1021/jo00031a019

Reference yield:

(±)-1-cyclohexyl-2-methylprop-2-en-1-ol (138490-37-6) → (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropanal (138490-51-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 91 percent / imidazole / dimethylformamide / 16 h / 25 °C

2: 1.) 9-BBN, 2.) 30percent H₂O₂, 6N aq. NaOH / 1.) THF, 16 h, -80 deg C to r.t., 2.) 2 h, -10 to 25 deg C

3: 88 percent / Bu₄N⁽¹⁺⁾F^(1-) / tetrahydrofuran / 16 h / 25 °C

4: 92 percent / trimethylsilyl trifluoromethanesulfonate (TMSOTf) / tetrahydrofuran / 1 h / 25 °C

5: trimethylsilyl trifluoromethanesulfonate (TMSOTf) / CH₂Cl₂ / 18 h / -40 °C

6: 85 percent / p-toluenesulfonic acid / methanol / Ambient temperature

7: 1.) oxalyl chloride, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -85 deg C, 20 min, 2.a) -85 deg C, 30 min, b) -85 deg C to r.t., 50 min

With 1H-imidazole; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; tetrabutyl ammonium fluoride; dihydrogen peroxide; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo00031a019

upstream raw materials:

(1R,2S)-1-cyclohexyl-2-methyl-1,3-propanediol

propionaldehyde

cyclohexanecarbaldehyde

(1R*,2S*)-1-cyclohexyl-2-methyl-1,3-bis(trimethylsiloxy)propane

Downstream raw materials:

(-)-methyl (2R,3R)-3-cyclohexyl-3-hydroxy-2-methylpropionate

(2R,3R)-3-Cyclohexyl-3-hydroxy-2-methyl-propionic acid