2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate

Base Information

• Chemical Name: 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate
• CAS No.: 331961-25-2
• Molecular Formula: C₂₁H₃₂O₅S
• Molecular Weight: 396.548

Synonyms:2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate

Chemical Property of 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate

There total 9 articles about 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate 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: 97.0%

p-toluenesulfonyl chloride (98-59-9) + 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethanol (331961-24-1) → 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate (331961-25-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 25 ℃; for 20h;

DOI:10.1002/1521-3765(20010119)7:2<520::AID-CHEM520>3.0.CO;2-5

Reference yield:

(6S,5R)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one (91781-46-3) → 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate (331961-25-2)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 80 percent / aq. NaHCO₃; sodium dithionite / Adogen 464 / toluene / 2 h / Heating

2.1: EtMgBr / toluene; tetrahydrofuran / 0 - 60 °C

2.2: toluene; tetrahydrofuran / 2 h / Heating

2.3: 44 percent / aq. H₂SO₄ / tetrahydrofuran / 10 h

3.1: Mg; methanol

4.1: 97 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

5.1: O₃ / CH₂Cl₂; methanol / -40 °C

5.2: 89 percent / dimethylsulfide / CH₂Cl₂; methanol / 25 °C

6.1: 83 percent / trimethylorthoformate; p-TsOH / 2 h / 25 °C

7.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 25 °C

With methanol; dmap; lithium aluminium tetrahydride; sodium dithionite; ethylmagnesium bromide; sodium hydrogencarbonate; toluene-4-sulfonic acid; ozone; magnesium; triethylamine; trimethyl orthoformate; adogen 464; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1002/1521-3765(20010119)7:2<520::AID-CHEM520>3.0.CO;2-5

Reference yield:

(2S,3R,6R)-2,6-dimethyl-3-(prop-1-en-2-yl)cyclohexan-1-one (331961-14-9) → 2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethyl toluene-4-sulfonate (331961-25-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: EtMgBr / toluene; tetrahydrofuran / 0 - 60 °C

1.2: toluene; tetrahydrofuran / 2 h / Heating

1.3: 44 percent / aq. H₂SO₄ / tetrahydrofuran / 10 h

2.1: Mg; methanol

3.1: 97 percent / LiAlH₄ / tetrahydrofuran / 3 h / 25 °C

4.1: O₃ / CH₂Cl₂; methanol / -40 °C

4.2: 89 percent / dimethylsulfide / CH₂Cl₂; methanol / 25 °C

5.1: 83 percent / trimethylorthoformate; p-TsOH / 2 h / 25 °C

6.1: 97 percent / Et₃N; DMAP / CH₂Cl₂ / 20 h / 25 °C

With methanol; dmap; lithium aluminium tetrahydride; ethylmagnesium bromide; toluene-4-sulfonic acid; ozone; magnesium; triethylamine; trimethyl orthoformate; In tetrahydrofuran; methanol; dichloromethane; toluene;

DOI:10.1002/1521-3765(20010119)7:2<520::AID-CHEM520>3.0.CO;2-5

upstream raw materials:

p-toluenesulfonyl chloride

2-[(1S,2R,3R,6R)-2,6-Dimethyl-3-(2-methyl-[1,3]-dioxolan-2-yl)cyclohexyl]ethanol

(6S,5R)-2,6-dimethyl-5-(1-methylethenyl)-2-cyclohexen-1-one

(2S,3R,6R)-2,6-dimethyl-3-(prop-1-en-2-yl)cyclohexan-1-one

Downstream raw materials:

(1R,2R,3S,4R)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarbaldehyde

1-[(1R,2R,3S,6R)-3-(5-Hydroxy-5-methylhexyl)-2,4-dimethylcyclohexyl]ethanone

6-((1S,2R,3R,6R)-3-Hydroxymethyl-2,6-dimethyl-cyclohexyl)-2-methyl-hexan-2-ol

(1R,2R,3S,4R)-3-(5-Hydroxy-5-methyl-hexyl)-2,4-dimethyl-cyclohexanecarboxylic acid methyl ester

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