(6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione

Base Information

• Chemical Name: (6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione
• CAS No.: 298713-15-2
• Molecular Formula: C₂₅H₃₆O₃S
• Molecular Weight: 416.625
• Mol file: 298713-15-2.mol

Synonyms:(6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione

Chemical Property of (6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione

There total 10 articles about (6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione 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:

Farnesol (106-28-5) → (6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione (298713-15-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 95 percent / H₂ / ((R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro(; p-cymene)ruthenium chloride / methanol / 24 h / 72402.6 Torr

2.1: 95 percent / pyridine / CH₂Cl₂ / 3 h / 0 °C

3.1: 71 percent / Me₂AlCl / CH₂Cl₂ / 0.25 h / -78 - 15 °C

4.1: 77 percent / oxalyl chloride; triethylamine; dimethylsulfoxide / CH₂Cl₂ / 5 h / 20 °C

5.1: 90 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / -20 °C

6.1: 77 percent / H₂ / ((S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro(; p-cymene)ruthenium chloride / methanol / 120 h / 87917.5 Torr

7.1: 91 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 0 - 23 °C

8.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C

8.2: hexane; tetrahydrofuran / 15.5 h / -78 - 0 °C

9.1: 62 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

10.1: tetrahydrofuran; diethyl ether; pentane / 0.5 h / -78 °C

10.2: tetrahydrofuran; diethyl ether; pentane / 1.5 h / -78 °C

10.3: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; hydrogen; dimethylaluminum chloride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; ((R)-(+)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro(; ((S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro(; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; pentane; 1.1: Hydrogenation / 2.1: Esterification / 3.1: Prins reaction / 4.1: Swern oxidation / 5.1: Reduction / 6.1: Hydrogenation / 7.1: Oxidation / 8.1: Metallation / 8.2: condensation / 9.1: Oxidation / 10.1: Metallation / 10.2: Alkylation / 10.3: Oxidation;

DOI:10.1021/ol006220z

Reference yield:

(3S)-(6E)-2,3-dihydrofarnesol (20576-54-9,34083-92-6,37519-97-4,51411-24-6,69686-26-6,69743-81-3,76190-00-6,113889-56-8,27745-36-4) → (6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione (298713-15-2)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 95 percent / pyridine / CH₂Cl₂ / 3 h / 0 °C

2.1: 71 percent / Me₂AlCl / CH₂Cl₂ / 0.25 h / -78 - 15 °C

3.1: 77 percent / oxalyl chloride; triethylamine; dimethylsulfoxide / CH₂Cl₂ / 5 h / 20 °C

4.1: 90 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / -20 °C

5.1: 77 percent / H₂ / ((S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro(; p-cymene)ruthenium chloride / methanol / 120 h / 87917.5 Torr

6.1: 91 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 0 - 23 °C

7.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C

7.2: hexane; tetrahydrofuran / 15.5 h / -78 - 0 °C

8.1: 62 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

9.1: tetrahydrofuran; diethyl ether; pentane / 0.5 h / -78 °C

9.2: tetrahydrofuran; diethyl ether; pentane / 1.5 h / -78 °C

9.3: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

With pyridine; sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; hydrogen; dimethylaluminum chloride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; ((S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro(; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; pentane; 1.1: Esterification / 2.1: Prins reaction / 3.1: Swern oxidation / 4.1: Reduction / 5.1: Hydrogenation / 6.1: Oxidation / 7.1: Metallation / 7.2: condensation / 8.1: Oxidation / 9.1: Metallation / 9.2: Alkylation / 9.3: Oxidation;

DOI:10.1021/ol006220z

Reference yield:

2,2-Dimethyl-propionic acid (E)-(S)-3,7,11-trimethyl-dodeca-6,10-dienyl ester (298713-06-1) → (6E)-(3S,10S)-1-benzenesulfinyl-6,10-dimethyl-3-isopropyl-6,13-tetradecadiene-2,12-dione (298713-15-2)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 71 percent / Me₂AlCl / CH₂Cl₂ / 0.25 h / -78 - 15 °C

2.1: 77 percent / oxalyl chloride; triethylamine; dimethylsulfoxide / CH₂Cl₂ / 5 h / 20 °C

3.1: 90 percent / NaBH₄; CeCl₃*7H₂O / methanol / 0.5 h / -20 °C

4.1: 77 percent / H₂ / ((S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro(; p-cymene)ruthenium chloride / methanol / 120 h / 87917.5 Torr

5.1: 91 percent / tetrapropylammonium perruthenate; N-methylmorpholine N-oxide; molecular sieves 4 Angstroem / CH₂Cl₂ / 1 h / 0 - 23 °C

6.1: LDA / tetrahydrofuran; hexane / 1 h / 0 °C

6.2: hexane; tetrahydrofuran / 15.5 h / -78 - 0 °C

7.1: 62 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 2 h / 0 °C

8.1: tetrahydrofuran; diethyl ether; pentane / 0.5 h / -78 °C

8.2: tetrahydrofuran; diethyl ether; pentane / 1.5 h / -78 °C

8.3: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

With sodium tetrahydroborate; cerium(III) chloride; tetrapropylammonium perruthennate; oxalyl dichloride; 4 A molecular sieve; hydrogen; dimethylaluminum chloride; sodium hydrogencarbonate; Dess-Martin periodane; dimethyl sulfoxide; 4-methylmorpholine N-oxide; triethylamine; lithium diisopropyl amide; [ruthenium(II)(η⁶-1-methyl-4-isopropyl-benzene)(chloride)(μ-chloride)]₂; ((S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl)chloro(; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; pentane; 1.1: Prins reaction / 2.1: Swern oxidation / 3.1: Reduction / 4.1: Hydrogenation / 5.1: Oxidation / 6.1: Metallation / 6.2: condensation / 7.1: Oxidation / 8.1: Metallation / 8.2: Alkylation / 8.3: Oxidation;

DOI:10.1021/ol006220z

upstream raw materials:

Vinyl bromide

(3S,10S,6E)-12-benzenesulfinyl-10-isopropyl-3,7-dimethyl-11-oxo-dodec-6-enal

Farnesol

(3S)-(6E)-2,3-dihydrofarnesol

Refernces