Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester
• CAS No.: 125975-54-4
• Molecular Formula: C₁₅H₂₀O₃S
• Molecular Weight: 280.388
• Mol file: 125975-54-4.mol

Synonyms:Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester

There total 7 articles about Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester 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: 90.0%

(1R,6S)-6-methyl-3-cyclohexenemethanol (102629-34-5) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester (125975-54-4)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 24h; Ambient temperature;

DOI:10.1021/ja00164a024

Reference yield:

5r-Methyl-4c-methoxycarbonylcyclohex-1-en (117065-52-8) → Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester (125975-54-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 99 percent / LiAlH₄ / tetrahydrofuran / 15 h / Heating

2: 90 percent / pyridine, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 24 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; In tetrahydrofuran; dichloromethane;

DOI:10.1021/ja00164a024

Reference yield:

(1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester (117065-50-6) → Toluene-4-sulfonic acid (1R,6S)-6-methyl-cyclohex-3-enylmethyl ester (125975-54-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / methanol; CH₂Cl₂ / 46 h / Heating

2: 1.) LDA, 2.) CH₃COOH / 1.) THF, -78 deg C, 45 min, 2.) -78 deg C

3: 99 percent / LiAlH₄ / tetrahydrofuran / 15 h / Heating

4: 90 percent / pyridine, 4-(dimethylamino)pyridine (DMAP) / CH₂Cl₂ / 24 h / Ambient temperature

With pyridine; dmap; lithium aluminium tetrahydride; acetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/ja00164a024

upstream raw materials:

(1R,6S)-6-methyl-3-cyclohexenemethanol

p-toluenesulfonyl chloride

5r-Methyl-4c-methoxycarbonylcyclohex-1-en

(1S,6S)-6-Methyl-cyclohex-3-enecarboxylic acid benzyl ester

Downstream raw materials:

((1S,6S)-6-Methyl-cyclohex-3-enyl)-acetonitrile

((1S,6S)-6-Methyl-cyclohex-3-enyl)-acetic acid

3-{(4R,6S)-6-[2-(tert-Butyl-diphenyl-silanyloxy)-ethyl]-2,2-dimethyl-[1,3]dioxan-4-yl}-2-((1R,2S,5S)-5-hydroxy-2-methyl-cyclohex-3-enyl)-propionaldehyde

<1S-<1α,4α-(4S^*,6R^*),5α,6β>>-4-<<6-<2-<<(1,1-dimethylethyl)diphenylsilyl>oxy>ethyl>-2,2-dimethyl-1,3-dioxan-4-yl>methyl>-6-methyl-2-oxabicyclo<3.3.1>non-7-en-3-one