(1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol

Base Information

• Chemical Name: (1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol
• CAS No.: 113161-40-3
• Molecular Formula: C₁₂H₂₂O₂
• Molecular Weight: 198.305
• Mol file: 113161-40-3.mol

Synonyms:(1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol

Chemical Property of (1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol

There total 11 articles about (1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol 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: 84.0%

(1S,4S,5S,8S)-4-Allyl-8-methyl-2-oxa-bicyclo[3.3.1]nonan-3-one (113161-39-0) → (1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol (113161-40-3)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 25 ℃; for 1h;

DOI:10.1021/jo00242a053

Reference yield:

(1S,2S,5S)-5-(1-hydroxypropan-2-yl)-2-methylcyclohexanol → (1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol (113161-40-3)

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine

2: pyridinium p-toluenesulfonate (PPTS) / CH₂Cl₂

3: aq. KOH

4: pyridinium chlorochromate (PCC) , NaOAc / CH₂Cl₂

5: NaClO₂, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O

6: aq. acetic acid / 80 °C

7: 67 percent / p-toluenesulfonic acid / toluene / Heating

8: lithium diisopropylamide (LDA) / hexamethylphosphoric acid triamide

9: H₂O₂

10: 79 percent / CuI, dimethyl sulfide, trimethylsilyl chloride / tetrahydrofuran / -40 °C

11: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

With pyridine; potassium hydroxide; sodium chlorite; copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; 2-methyl-but-2-ene; dimethylsulfide; dihydrogen peroxide; sodium acetate; pyridinium p-toluenesulfonate; toluene-4-sulfonic acid; acetic acid; pyridinium chlorochromate; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; toluene; tert-butyl alcohol;

DOI:10.1021/jo00242a053

Reference yield:

(1S,5S,8S)-4,8-Dimethyl-2-oxa-bicyclo[3.3.1]nonan-3-one → (1S,2S,5S)-5-((S)-1-Hydroxymethyl-but-3-enyl)-2-methyl-cyclohexanol (113161-40-3)

Guidance literature:

Multi-step reaction with 4 steps

1: lithium diisopropylamide (LDA) / hexamethylphosphoric acid triamide

2: H₂O₂

3: 79 percent / CuI, dimethyl sulfide, trimethylsilyl chloride / tetrahydrofuran / -40 °C

4: 84 percent / LiAlH₄ / tetrahydrofuran / 1 h / 25 °C

With copper(l) iodide; lithium aluminium tetrahydride; chloro-trimethyl-silane; dimethylsulfide; dihydrogen peroxide; lithium diisopropyl amide; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide;

DOI:10.1021/jo00242a053

upstream raw materials:

(1S,4S,5S,8S)-4-Allyl-8-methyl-2-oxa-bicyclo[3.3.1]nonan-3-one

(1S,5S,8S)-8-Methyl-4-methylene-2-oxa-bicyclo[3.3.1]nonan-3-one

Downstream raw materials:

(2S,5S)-2-Methyl-5-((S)-1-methyl-but-3-enyl)-cyclohexanone

(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-ol

Formic acid (4S,6S,6aR,9S)-2-benzyloxy-4-formyl-3,6,9-trimethyl-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yl ester

(2S,3R,4S,5R)-2-[(4R,6S,6aR,9S)-2-Benzyloxy-3,6,9-trimethyl-4-(2-methyl-propenyl)-5,6,6a,7,8,9-hexahydro-4H-phenalen-1-yloxy]-tetrahydro-pyran-3,4,5-triol