(1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol

Base Information

• Chemical Name: (1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol
• CAS No.: 199661-63-7
• Molecular Formula: C₁₃H₂₂O₂
• Molecular Weight: 210.316
• Mol file: 199661-63-7.mol

Synonyms:(1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol

Chemical Property of (1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol

There total 1 articles about (1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol 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: 99.0%

(3R,3aR,4R,7aS)-4-Isopropenyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one (158690-89-2) → (1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol (199661-63-7)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at -78 - -20 ℃; for 3h;

DOI:10.3891/acta.chem.scand.51-1217

Reference yield: 86.0%

pivaloyl chloride (3282-30-2) + (1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol (199661-63-7) → 2,2-Dimethyl-propionic acid (R)-2-((1R,2S,6R)-2-hydroxy-6-isopropenyl-4-methyl-cyclohex-3-enyl)-propyl ester (199661-64-8)

Guidance literature:

In pyridine; for 1h; Ambient temperature;

DOI:10.3891/acta.chem.scand.51-1217

Reference yield:

(1S,5R,6R)-6-((R)-2-Hydroxy-1-methyl-ethyl)-5-isopropenyl-3-methyl-cyclohex-2-enol (199661-63-7) → (R)-2-((1R,2S,6R)-6-Isopropenyl-2-methoxymethoxy-4-methyl-cyclohex-3-enyl)-propan-1-ol (199661-66-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 86 percent / pyridine / 1 h / Ambient temperature

2: 88 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h

3: 99 percent / 1M DIBAL / CH₂Cl₂; hexane / 0.5 h / -78 °C

With diisobutylaluminium hydride; N-ethyl-N,N-diisopropylamine; In pyridine; hexane; dichloromethane;

DOI:10.3891/acta.chem.scand.51-1217

upstream raw materials:

(3R,3aR,4R,7aS)-4-Isopropenyl-3,6-dimethyl-3a,4,5,7a-tetrahydro-3H-benzofuran-2-one

Downstream raw materials:

2,2-Dimethyl-propionic acid (R)-2-((1R,2S,6R)-2-hydroxy-6-isopropenyl-4-methyl-cyclohex-3-enyl)-propyl ester

(R)-2-((1R,2S,6R)-6-Isopropenyl-2-methoxymethoxy-4-methyl-cyclohex-3-enyl)-propan-1-ol

(R)-2-((1R,2S,6R)-6-Isopropenyl-2-methoxymethoxy-4-methyl-cyclohex-3-enyl)-propionaldehyde

2,2-Dimethyl-propionic acid (R)-2-((1R,2S,6R)-6-isopropenyl-2-methoxymethoxy-4-methyl-cyclohex-3-enyl)-propyl ester