(-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate

Base Information

• Chemical Name: (-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate
• CAS No.: 105996-71-2
• Molecular Formula: C₁₇H₂₄O₄S
• Molecular Weight: 324.441
• Mol file: 105996-71-2.mol

Synonyms:(-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate

Chemical Property of (-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate

There total 12 articles about (-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate 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:

2,2-dimethyl-1,3-cyclohexanedione (562-13-0) → (-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate (105996-71-2)

Guidance literature:

Multi-step reaction with 11 steps

1: 79 percent / H₂O / 48 h / 30 °C / fermentation, baker's yeast

2: p-TsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

3: 1.) NaOMe / 1.)THF, benzene, 10 min, 6 deg C 2.) RT, overnight

4: 6.9 g / p-TsOH / benzene / 3.5 h / Heating

5: p-TsOH / CH₂Cl₂ / Ambient temperature

6: 19.5 g / NaBH₄ / tetrahydrofuran; ethanol / 1.5 h / 0 - 4 °C

7: 14.1 g / CdCO₃, HgCl₂ / aq. ethanol / 0.03 h / Heating

8: 66 percent / NaBH₄ / aq. ethanol; tetrahydrofuran / 1 h / 0 - 5 °C

9: 1.) (n-Bu)3SnCH₂I 2.) n-BuLi / 1.) THF,DMF,44 h, RT 2.) THF, n-hexane, 1 h -65 deg C

10: 10.8 g / pyridine / 6 h / 0 - 5 °C

11: 6.86 g / p-TsOH / methanol / 1.17 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; sodium methylate; tri-n-butylstannylmethyl iodide; toluene-4-sulfonic acid; mercury dichloride; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; benzene;

DOI:10.1016/S0040-4020(01)91348-1

Reference yield:

(S)-3-hydroxy-2,2-dimethylcyclohexanone (87655-21-8) → (-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate (105996-71-2)

Guidance literature:

Multi-step reaction with 10 steps

1: p-TsOH / CH₂Cl₂ / 0.5 h / Ambient temperature

2: 1.) NaOMe / 1.)THF, benzene, 10 min, 6 deg C 2.) RT, overnight

3: 6.9 g / p-TsOH / benzene / 3.5 h / Heating

4: p-TsOH / CH₂Cl₂ / Ambient temperature

5: 19.5 g / NaBH₄ / tetrahydrofuran; ethanol / 1.5 h / 0 - 4 °C

6: 14.1 g / CdCO₃, HgCl₂ / aq. ethanol / 0.03 h / Heating

7: 66 percent / NaBH₄ / aq. ethanol; tetrahydrofuran / 1 h / 0 - 5 °C

8: 1.) (n-Bu)3SnCH₂I 2.) n-BuLi / 1.) THF,DMF,44 h, RT 2.) THF, n-hexane, 1 h -65 deg C

9: 10.8 g / pyridine / 6 h / 0 - 5 °C

10: 6.86 g / p-TsOH / methanol / 1.17 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; sodium methylate; tri-n-butylstannylmethyl iodide; toluene-4-sulfonic acid; mercury dichloride; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)91348-1

Reference yield:

(3S)-6-formyl-2,2-dimethyl-3-tetrahydropyranyloxycyclohexanone (105996-61-0) → (-)-(1S,3S)-(3-hydroxy-2,2-dimethyl-6-methylenecyclohexyl)methyl p-toluenesulfonate (105996-71-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 6.9 g / p-TsOH / benzene / 3.5 h / Heating

2: p-TsOH / CH₂Cl₂ / Ambient temperature

3: 19.5 g / NaBH₄ / tetrahydrofuran; ethanol / 1.5 h / 0 - 4 °C

4: 14.1 g / CdCO₃, HgCl₂ / aq. ethanol / 0.03 h / Heating

5: 66 percent / NaBH₄ / aq. ethanol; tetrahydrofuran / 1 h / 0 - 5 °C

6: 1.) (n-Bu)3SnCH₂I 2.) n-BuLi / 1.) THF,DMF,44 h, RT 2.) THF, n-hexane, 1 h -65 deg C

7: 10.8 g / pyridine / 6 h / 0 - 5 °C

8: 6.86 g / p-TsOH / methanol / 1.17 h / Ambient temperature

With sodium tetrahydroborate; n-butyllithium; cadmium(II) carbonate; tri-n-butylstannylmethyl iodide; toluene-4-sulfonic acid; mercury dichloride; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)91348-1

upstream raw materials:

p-toluenesulfonyl chloride

2,2-dimethyl-1,3-cyclohexanedione

(S)-3-hydroxy-2,2-dimethylcyclohexanone

(S)-6-[1-Butylsulfanyl-meth-(E)-ylidene]-3-hydroxy-2,2-dimethyl-cyclohexanone

Downstream raw materials:

(1S,3S)-(+)-2,2-dimethyl-6-methylene-3-tosyloxycyclohexanemethyl formate

(+)-(1S,3S)-(2,2-dimethyl-6-methylene-3-p-toluenesulfonyloxycyclohexyl)methyl p-toluenesulfonate