2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene

Base Information

Chemical Name:2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene
CAS No.:247067-40-9
Molecular Formula:C₂₉H₄₆O₂SSi
Molecular Weight:486.835
Hs Code.:

Synonyms:2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene

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Chemical Property of 2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene

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Technology Process of 2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene

There total 11 articles about 2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene 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: 98.0%

: 75-77-4
chloro-trimethyl-silane

: 132274-03-4
(2R,3R,all-E)-2,3-Epoxy-2,6,10,14-tetramethyl-16-(phenylthio)hexadeca-6,10,14-trien-1-ol

: 247067-40-9
2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 10h;
DOI:10.1016/S0957-4166(99)00194-9

Reference yield:

: 6138-90-5
trans-geranyl bromide

: 247067-40-9
2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene

Guidance literature:: Multi-step reaction with 7 steps

1: dimethylformamide / 24 h / Ambient temperature

2: 78 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 25 h / 20 °C

3: 1.) Ti(OiPr)4, CaH₂, 4A molecular sieves, D-(-)-DET, 2.) tert-BuOOH / 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, toluene, -40 deg C, 5 h

4: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h

5: 78 percent / Li, EtNH₂ / tetrahydrofuran / 4 h / -78 °C

6: 1.) Ph₃P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h

7: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N-chloro-succinimide; selenium(IV) oxide; calcium hydride; diethyl (2S,3S)-tartrate; 4 A molecular sieve; lithium; ethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(99)00194-9

Reference yield:

: 106-24-1
Geraniol

: 247067-40-9
2,6,10,14-tetramethyl-1-(trimethylsiloxy)-2R,3R-epoxy-16-(thiophenyl)-6E,10E,14E-hexadecatriene

Guidance literature:: Multi-step reaction with 8 steps

1: PBr₃ / diethyl ether / 3 h / 20 °C

2: dimethylformamide / 24 h / Ambient temperature

3: 78 percent / SeO₂, t-BuOOH / CH₂Cl₂ / 25 h / 20 °C

4: 1.) Ti(OiPr)4, CaH₂, 4A molecular sieves, D-(-)-DET, 2.) tert-BuOOH / 1.) CH₂Cl₂, -20 deg C, 15 min, 2.) CH₂Cl₂, toluene, -40 deg C, 5 h

5: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, from -78 deg C to RT, 2 h

6: 78 percent / Li, EtNH₂ / tetrahydrofuran / 4 h / -78 °C

7: 1.) Ph₃P, N-chlorosuccinimide / 1.) THF, 20 deg C, 5 h, 2.) THF, 3 h

8: 98 percent / imidazole / dimethylformamide / 10 h / 50 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; N-chloro-succinimide; selenium(IV) oxide; calcium hydride; diethyl (2S,3S)-tartrate; 4 A molecular sieve; phosphorus tribromide; lithium; ethylamine; triphenylphosphine; lithium diisopropyl amide; In tetrahydrofuran; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1016/S0957-4166(99)00194-9