Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester
• CAS No.: 275825-13-3
• Molecular Formula: C₂₇H₄₀O₃S
• Molecular Weight: 444.679
• Mol file: 275825-13-3.mol

Synonyms:Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester

Chemical Property of Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester

There total 14 articles about Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl 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: 89.0%

p-toluenesulfonyl chloride (98-59-9) + [(1S,2R,5S,8aR)-1,2,5-Trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol (275825-08-6) → Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester (275825-13-3)

Guidance literature:

In pyridine; at 0 ℃;

DOI:10.1016/S0040-4039(00)00078-2

Reference yield:

(S)-6-methyl-6-(4-methylpent-4-en-1-yl)-1-vinylcyclohex-1-ene (275825-03-1) → Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester (275825-13-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: EtAlCl₂*THF / CH₂Cl₂ / -30 - 0 °C

1.2: 25 percent / AlH₃ / tetrahydrofuran / 0 °C

2.1: TPAP; NMO; MS 4A / 20 °C

2.2: tBuOK / tetrahydrofuran / 20 °C

2.3: 16 percent / NaBH₄; MeOH / 0 °C

3.1: pyridine / 0 °C

With pyridine; N-methyl-2-indolinone; tetrapropylammonium perruthennate; ethylaluminum dichloride; In dichloromethane; 1.1: Cycloaddition / 2.1: Oxidation / 3.1: Tosylation;

DOI:10.1016/S0960-894X(00)00527-8

Reference yield:

(S)-3-(1-methyl-2-oxocyclohexyl)-propionic acid methyl ester (53068-89-6,94089-47-1,150927-14-3,112898-44-9) → Toluene-4-sulfonic acid (1R,2R,5S,8aR)-1,2,5-trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-ylmethyl ester (275825-13-3)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 96 percent / benzene / Heating

2.1: 90 percent / LiAlH₄ / tetrahydrofuran / 0 °C

3.1: 92 percent / pyridine / 0 °C

4.1: 90 percent / NaI / acetone / Heating

5.1: 92 percent / CuI / tetrahydrofuran / -30 - 0 °C

6.1: 94 percent / pyridinium p-toluenesulfonate / acetone / Heating

7.1: CeCl₃ / tetrahydrofuran / 20 °C

7.2: CuSO₄ / benzene / Heating

8.1: 83 percent / EtAlCl₂*THF / CH₂Cl₂ / -30 - 0 °C

9.1: AlH₃ / tetrahydrofuran / 0 °C

10.1: 90 percent / TPAP; NMO; MS₄A / 20 °C

11.1: 80 percent / t-BuOK / tetrahydrofuran / 20 °C

12.1: NaBH₄ / methanol / 0 °C

13.1: 89 percent / pyridine / 0 °C

With aluminium hydride; sodium tetrahydroborate; lithium aluminium tetrahydride; N-methyl-2-indolinone; cerium(III) chloride; tetrapropylammonium perruthennate; potassium tert-butylate; pyridinium p-toluenesulfonate; sodium iodide; copper(l) iodide; ethylaluminum dichloride; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetone; benzene; 1.1: cyclocondensation / 2.1: Reduction / 3.1: Tosylation / 4.1: Substitution / 5.1: Grignard reaction / 6.1: Hydrolysis / 7.1: Grignard reaction / 7.2: Dehydration / 8.1: Diels-Alder reaction / 9.1: Reduction / 10.1: Oxidation / 11.1: Methylation / 12.1: Reduction / 13.1: Tosylation;

DOI:10.1016/S0040-4039(00)00078-2

upstream raw materials:

p-toluenesulfonyl chloride

[(1S,2R,5S,8aR)-1,2,5-Trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol

[(1R,2R,5S,8aR)-1,2,5-Trimethyl-5-(4-methyl-pent-4-enyl)-1,2,3,5,6,7,8,8a-octahydro-naphthalen-1-yl]-methanol

(S)-6-methyl-6-(4-methylpent-4-en-1-yl)-1-vinylcyclohex-1-ene