(1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol

Base Information

• Chemical Name: (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol
• CAS No.: 79563-67-0
• Molecular Formula: C₁₀H₂₀OS
• Molecular Weight: 188.334
• Mol file: 79563-67-0.mol

Synonyms:(1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol

Chemical Property of (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol

There total 4 articles about (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol 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: 59.0%

(2R,5R)-2-[1-(4-Heptyl-benzylsulfanyl)-1-methyl-ethyl]-5-methyl-cyclohexanone (407619-28-7) → (-)-(1R,2R,5R)-5-methyl-2-(1-mercapto-1-methylethyl)-cyclohexan-1-ol (79563-59-0) + (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol (79563-67-0)

Guidance literature:

(2R,5R)-2-[1-(4-Heptyl-benzylsulfanyl)-1-methyl-ethyl]-5-methyl-cyclohexanone; With lithium aluminium tetrahydride; In tetrahydrofuran;

With sodium; In ammonia;

DOI:10.1016/S0040-4039(01)02024-X

Reference yield:

5-methyl-2-<1-methyl-1-(benzylthio)ethyl>cyclohexanone (898541-20-3) → (-)-(1R,2R,5R)-5-methyl-2-(1-mercapto-1-methylethyl)-cyclohexan-1-ol (79563-59-0) + (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol (79563-67-0) + (1R,2S,5R)-2-(1-Mercapto-1-methyl-ethyl)-5-methyl-cyclohexanol (79563-68-1)

Guidance literature:

With methanol; sodium; In diethyl ether; ammonia; at -78 - -42 ℃; Yield given; 1.) -78 deg C, 5.5h; 2.) add MeOH, warm to -42 deg C until deep blue colour discharges;

DOI:10.1016/S0040-4039(01)81768-8

Reference yield:

pulegone (89-82-7,90449-51-7) → (1S,2R,5R)-2-(1-mercapto-1-methylethyl)-5-methylcyclohexanol (79563-67-0)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / aq. NaOH / tetrahydrofuran / 20 °C

2.1: LAH / tetrahydrofuran

2.2: 59 percent / Na; liq. NH₃ / tetrahydrofuran

With sodium hydroxide; lithium aluminium tetrahydride; In tetrahydrofuran; 1.1: Michael addition;

DOI:10.1007/s00706-003-0122-1

upstream raw materials:

5-methyl-2-<1-methyl-1-(benzylthio)ethyl>cyclohexanone

(2R,5R)-2-(1-Benzylsulfanyl-1-methyl-ethyl)-5-methyl-cyclohexanone

(2R,5R)-2-[1-(4-Heptyl-benzylsulfanyl)-1-methyl-ethyl]-5-methyl-cyclohexanone

pulegone