(-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate

Base Information

• Chemical Name: (-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate
• CAS No.: 1197850-85-3
• Molecular Formula: C₁₅H₂₆O₃
• Molecular Weight: 254.37
• Mol file: 1197850-85-3.mol

Synonyms:(-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate

Chemical Property of (-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate

There total 4 articles about (-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate 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: 91.0%

(-)-(1S,6R)-6-((R)-1-hydroxypropan-2-yl)-3-methylcyclohex-2-enol (1197850-78-4) + pivaloyl chloride (3282-30-2) → (-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate (1197850-85-3)

Guidance literature:

With pyridine; dmap; at 0 ℃; for 2h; Inert atmosphere;

DOI:10.1021/ol302106y

Reference yield:

methyl 2-((S)-4-methylcyclohex-3-enyl)propanoate → (-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate (1197850-85-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

2.1: diphenyl diselenide; sodium tetrahydroborate / methanol / 3 h / 20 - 65 °C / Inert atmosphere

2.2: 12 h / 0 - 65 °C / Inert atmosphere

3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere

4.1: dmap; pyridine / 2 h / 0 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; disodium hydrogenphosphate; lithium aluminium tetrahydride; diphenyl diselenide; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ol302106y

Reference yield:

methyl 2-((3S)-6-methyl-7-oxa-bicyclo[4.1.0]heptan-3-yl)propanoate (1394254-54-6) → (-)-(R)-2-((1R,2S)-2-hydroxy-4-methylcyclohex-3-enyl)propyl 2,2-dimethyl propanoate (1197850-85-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: diphenyl diselenide; sodium tetrahydroborate / methanol / 3 h / 20 - 65 °C / Inert atmosphere

1.2: 12 h / 0 - 65 °C / Inert atmosphere

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 °C / Inert atmosphere

3.1: dmap; pyridine / 2 h / 0 °C / Inert atmosphere

With pyridine; dmap; sodium tetrahydroborate; lithium aluminium tetrahydride; diphenyl diselenide; In tetrahydrofuran; methanol;

DOI:10.1021/ol302106y

upstream raw materials:

methyl 2-((3S)-6-methyl-7-oxa-bicyclo[4.1.0]heptan-3-yl)propanoate

(3R,3aR,7aS)-3,6-dimethyl-3,3a,4,5-tetrahydrobenzofuran-2(7aH)-one

(-)-(1S,6R)-6-((R)-1-hydroxypropan-2-yl)-3-methylcyclohex-2-enol

pivaloyl chloride

Downstream raw materials:

(-)-(R)-2-[(1R,2S)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-methylcyclohex-3-enyl]propan-1-ol

(-)-(R)-2-[(1R,2S)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-methylcyclohex-3-enyl]propanal

(-)-(R)-2-[(1R,2S)-2-[(1,1-dimethylethyl)dimethylsilyloxy]-4-methylcyclohex-3-enyl]propyl 2,2-dimethyl propanoate