(-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate

Base Information

Chemical Name:(-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate
CAS No.:142720-48-7
Molecular Formula:C₃₀H₄₆O₃Si
Molecular Weight:482.779
Hs Code.:

Synonyms:(-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate

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Chemical Property of (-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate

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Technology Process of (-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate

There total 12 articles about (-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate 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:

: 53254-60-7
3,7-dimethyl-1-(p-toluenesulfonyl)-2(E),6-octadiene

: 142720-48-7
(-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) tert-BuOOH, 2.) NaBH₄ / 1.) SeO₂, salicylic acid / 1.) CH₂Cl₂, room temperature, 24 h, 2.) abs. ethanol, 0 deg C, 15 min

2: t-BuOOH, powered activated 4-Angstroem molecular sieves / (+)-diisopropyl L-tartrate, titanium(IV) isopropoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3.5 h / -23 °C

3: 98 percent / pyridine / CHCl₃ / 2.5 h / 0 °C

4: 57 percent / lithium triethylborohydride / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 15 min

5: 1.) n-butyllithium / 1.) THF/HMPA, hexane, a) -78 deg C, 15 min, b) -23 deg C, 1 h, 2.) THF, a) -78 deg C, 2 h, b) -23 deg C, 2 h

6: 1.) lithium, ethylamine, 2.) pyridine / 2.) 4-(dimethylamino)pyridine / 1.) ether, -78 deg C, 45 min, 2.) room temperature, 4 h

With pyridine; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; lithium; lithium triethylborohydride; ethylamine; titanium(IV) isopropylate; dmap; selenium(IV) oxide; L-(+)-diisopropyl tartrate; salicylic acid; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; chloroform;
DOI:10.1021/jo00043a014

Reference yield:

: 70238-35-6
(2E,6E)-3,7-dimethyl-1-(4-methylbenzenesulfonyl)-2,6-octadien-8-ol

: 142720-48-7
(-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate

Guidance literature:: Multi-step reaction with 5 steps

1: t-BuOOH, powered activated 4-Angstroem molecular sieves / (+)-diisopropyl L-tartrate, titanium(IV) isopropoxide / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3.5 h / -23 °C

2: 98 percent / pyridine / CHCl₃ / 2.5 h / 0 °C

3: 57 percent / lithium triethylborohydride / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 15 min

4: 1.) n-butyllithium / 1.) THF/HMPA, hexane, a) -78 deg C, 15 min, b) -23 deg C, 1 h, 2.) THF, a) -78 deg C, 2 h, b) -23 deg C, 2 h

5: 1.) lithium, ethylamine, 2.) pyridine / 2.) 4-(dimethylamino)pyridine / 1.) ether, -78 deg C, 45 min, 2.) room temperature, 4 h

With pyridine; tert.-butylhydroperoxide; n-butyllithium; 4 A molecular sieve; lithium; lithium triethylborohydride; ethylamine; titanium(IV) isopropylate; dmap; L-(+)-diisopropyl tartrate; In tetrahydrofuran; 2,2,4-trimethylpentane; dichloromethane; chloroform;
DOI:10.1021/jo00043a014

Reference yield:

: 110481-61-3
3-trimethylsilyl-2-diethylphosphonopropionic acid ethyl ester

: 142720-48-7
(-)-(14S,2E,6E,10E)-14,15-epoxy-3,11,15-trimethyl-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatrienyl benzoate

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) KH, 2.) 18-crown-6 / 1.) THF, 0 deg C, 1.5 h, 2.) THF, -78 deg C, 6 h

2: 91 percent / AlCl₃, LiAlH₄ / diethyl ether / 5 h / 0 °C

3: 98 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

4: 98 percent / LiBr / dimethylformamide / 2 h / 0 °C

5: 1.) n-butyllithium / 1.) THF/HMPA, hexane, a) -78 deg C, 15 min, b) -23 deg C, 1 h, 2.) THF, a) -78 deg C, 2 h, b) -23 deg C, 2 h

6: 1.) lithium, ethylamine, 2.) pyridine / 2.) 4-(dimethylamino)pyridine / 1.) ether, -78 deg C, 45 min, 2.) room temperature, 4 h

With pyridine; lithium aluminium tetrahydride; n-butyllithium; aluminium trichloride; 18-crown-6 ether; lithium; potassium hydride; ethylamine; triethylamine; lithium bromide; dmap; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/jo00043a014