(9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene

Base Information

Chemical Name:(9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene
CAS No.:142720-45-4
Molecular Formula:C₃₇H₅₄O₄SSi
Molecular Weight:622.985
Hs Code.:

(9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene

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Chemical Property of (9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene

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Technology Process of (9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene

There total 17 articles about (9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-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:

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

: 142720-45-4,142720-46-5,142793-48-4,142793-49-5
(9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene

Guidance literature:: Multi-step reaction with 5 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

With pyridine; tert.-butylhydroperoxide; sodium tetrahydroborate; n-butyllithium; 4 A molecular sieve; lithium triethylborohydride; titanium(IV) isopropylate; 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

: 142720-45-4,142720-46-5,142793-48-4,142793-49-5
(9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene

Guidance literature:: Multi-step reaction with 4 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

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

Reference yield:

: (E)-4-Methyl-6-(toluene-4-sulfonyl)-hex-4-enal

: 142720-45-4,142720-46-5,142793-48-4,142793-49-5
(9S/9R,14S,2E,6E,10E)-1-(benzyloxy)-14,15-epoxy-3,11,15-trimethyl-9-(4-methylbenzenesulfonyl)-7-<(trimethylsilyl)methyl>-2,6,10-hexadecatriene

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / CH₂Cl₂ / Heating

2: 87 percent / AlCl₃, LiAlH₄ / diethyl ether / 5 h / 0 °C

3: 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

4: 98 percent / pyridine / CHCl₃ / 2.5 h / 0 °C

5: 57 percent / lithium triethylborohydride / tetrahydrofuran / 1.) 0 deg C, 15 min, 2.) room temperature, 15 min

6: 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

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