(2S,6R)-2,6-dimethyl-14-pentadecenyl tosylate

Base Information

Chemical Name:(2S,6R)-2,6-dimethyl-14-pentadecenyl tosylate
CAS No.:299430-10-7
Molecular Formula:C₂₄H₄₀O₃S
Molecular Weight:408.646
Hs Code.:

Synonyms:(2S,6R)-2,6-dimethyl-14-pentadecenyl tosylate

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Chemical Property of (2S,6R)-2,6-dimethyl-14-pentadecenyl tosylate

Chemical Property:

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Technology Process of (2S,6R)-2,6-dimethyl-14-pentadecenyl tosylate

There total 7 articles about (2S,6R)-2,6-dimethyl-14-pentadecenyl 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%

: 98-59-9
p-toluenesulfonyl chloride

: 299430-09-4
(2S,6R)-2,6-dimethyl-14-pentadecen-1-ol

: 299430-10-7
(2S,6R)-2,6-dimethyl-14-pentadecenyl tosylate

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:

: 299430-04-9
(S)-2-methyl-4-phenylsulfonyl-1-tetrahydropyranyloxybutane

: 299430-10-7
(2S,6R)-2,6-dimethyl-14-pentadecenyl tosylate

Guidance literature:: Multi-step reaction with 7 steps

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

1.2: 88 percent / tetrahydrofuran; hexamethylphosphoric acid triamide; hexane / 10 h / 20 °C

2.1: 87 percent / 5 percent sodium amalgam; EtOH / 26 h / 20 °C

3.1: 99 percent / n-Bu₄NF / tetrahydrofuran / 4 h / 20 °C

4.1: 100 percent / pyridine / 12 h / 0 °C

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

5.2: 88 percent / Li₂CuCl₄ / tetrahydrofuran / 17 h / -78 - 0 °C

6.1: 96 percent / p-TsOH*H₂O / aq. ethanol / 3 h / Heating

7.1: 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; 1.1: Metallation / 1.2: Alkylation / 2.1: Reduction / 3.1: desilylation / 4.1: Tosylation / 5.1: Grignard reaction / 5.2: Alkylation / 6.1: Hydrolysis / 7.1: Tosylation;
DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I

Reference yield:

: 299430-03-8
(2S,6S)-2,6-dimethyl-7-tetrahydropyranyloxy-1-heptanol

: 299430-10-7
(2S,6R)-2,6-dimethyl-14-pentadecenyl tosylate

Guidance literature:: Multi-step reaction with 4 steps

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

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

2.2: 88 percent / Li₂CuCl₄ / tetrahydrofuran / 17 h / -78 - 0 °C

3.1: 96 percent / p-TsOH*H₂O / aq. ethanol / 3 h / Heating

4.1: 100 percent / pyridine / 12 h / 0 °C

With toluene-4-sulfonic acid; magnesium; In tetrahydrofuran; pyridine; ethanol; 1.1: Tosylation / 2.1: Grignard reaction / 2.2: Alkylation / 3.1: Hydrolysis / 4.1: Tosylation;
DOI:10.1002/1099-0690(200008)2000:15<2745::AID-EJOC2745>3.0.CO;2-I