(2R,6S)-2,6-dimethyltetradecyl tosylate

Base Information

• Chemical Name: (2R,6S)-2,6-dimethyltetradecyl tosylate
• CAS No.: 299430-29-8
• Molecular Formula: C₂₃H₄₀O₃S
• Molecular Weight: 396.635
• Mol file: 299430-29-8.mol

Synonyms:(2R,6S)-2,6-dimethyltetradecyl tosylate

Chemical Property of (2R,6S)-2,6-dimethyltetradecyl tosylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,6S)-2,6-dimethyltetradecyl tosylate

There total 10 articles about (2R,6S)-2,6-dimethyltetradecyl tosylate 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: 100.0%

p-toluenesulfonyl chloride (98-59-9) + (2R,6S)-2,6-dimethyl-1-tetradecanol (299430-28-7) → (2R,6S)-2,6-dimethyltetradecyl tosylate (299430-29-8)

Guidance literature:

In pyridine; at 0 ℃; for 12h;

DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield:

(R)-3-Methyl-4-<(tetrahydropyranyl)oxy>-1-iodobutane (299430-07-2) → (2R,6S)-2,6-dimethyltetradecyl tosylate (299430-29-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 85 percent / dimethylformamide / 12 h / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -30 °C

2.2: 91 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h / 20 °C

3.1: 82 percent / 5 percent sodium amalgam; EtOH / 26 h / 20 °C

4.1: 99 percent / n-Bu₄NF / tetrahydrofuran / 4 h / 20 °C

5.1: 100 percent / pyridine / 12 h / 0 °C

6.1: Mg / tetrahydrofuran / 1 h / 45 °C

6.2: 89 percent / Li₂CuCl₄ / tetrahydrofuran / 22 h / -78 - 0 °C

7.1: 97 percent / p-TsOH*H₂O / aq. ethanol / 3 h / Heating

8.1: 100 percent / pyridine / 12 h / 0 °C

With sodium amalgam; n-butyllithium; ethanol; tetrabutyl ammonium fluoride; toluene-4-sulfonic acid; magnesium; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; N,N-dimethyl-formamide; 1.1: Alkylation / 2.1: Metallation / 2.2: Alkylation / 3.1: Reduction / 4.1: desilylation / 5.1: Tosylation / 6.1: Grignard reaction / 6.2: Alkylation / 7.1: Hydrolysis / 8.1: Tosylation;

DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield:

(R)-3-Methyl-4-<(tetrahydropyranyl)oxy>butan-1-ol (170717-85-8) → (2R,6S)-2,6-dimethyltetradecyl tosylate (299430-29-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 100 percent / pyridine / 12 h / 0 °C

2.1: 93 percent / NaI; NaHCO₃ / acetone / 4 h / Heating

3.1: 85 percent / dimethylformamide / 12 h / 20 °C

4.1: n-BuLi / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 1 h / -30 °C

4.2: 91 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h / 20 °C

5.1: 82 percent / 5 percent sodium amalgam; EtOH / 26 h / 20 °C

6.1: 99 percent / n-Bu₄NF / tetrahydrofuran / 4 h / 20 °C

7.1: 100 percent / pyridine / 12 h / 0 °C

8.1: Mg / tetrahydrofuran / 1 h / 45 °C

8.2: 89 percent / Li₂CuCl₄ / tetrahydrofuran / 22 h / -78 - 0 °C

9.1: 97 percent / p-TsOH*H₂O / aq. ethanol / 3 h / Heating

10.1: 100 percent / pyridine / 12 h / 0 °C

With sodium amalgam; n-butyllithium; ethanol; tetrabutyl ammonium fluoride; sodium hydrogencarbonate; toluene-4-sulfonic acid; magnesium; sodium iodide; In tetrahydrofuran; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; ethanol; hexane; N,N-dimethyl-formamide; acetone; 1.1: Tosylation / 2.1: Substitution / 3.1: Alkylation / 4.1: Metallation / 4.2: Alkylation / 5.1: Reduction / 6.1: desilylation / 7.1: Tosylation / 8.1: Grignard reaction / 8.2: Alkylation / 9.1: Hydrolysis / 10.1: Tosylation;

DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

upstream raw materials:

p-toluenesulfonyl chloride

(2R,6S)-2,6-dimethyl-1-tetradecanol

(R)-3-Methyl-4-<(tetrahydropyranyl)oxy>-1-iodobutane

(R)-3-Methyl-4-<(tetrahydropyranyl)oxy>butan-1-ol

Downstream raw materials:

(5S,9S)-5,9-Dimethylheptadecane