(1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene

Base Information

Chemical Name:(1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene
CAS No.:640270-58-2
Molecular Formula:C₃₃H₄₁BrO₃Si
Molecular Weight:593.676
Hs Code.:

Synonyms:(1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene

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Technology Process of (1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene

There total 8 articles about (1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene 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: 85.0%

: 377751-03-6
(3S,4R,6E)-1,1-dibromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene

: 640270-58-2
(1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene

Guidance literature:: With palladium diacetate; tri-n-butyl-tin hydride; triphenylphosphine; In toluene; at 20 ℃; for 0.5h;
DOI:10.1021/ja038732p

Reference yield:

: 377751-07-0
(2E,5R,6S)-6,7-(isopropylidene)dioxy-5-methyl-2-hepten-1-ol

: 640270-58-2
(1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene

Guidance literature:: Multi-step reaction with 7 steps

1: Amberlyst 15 / aq. methanol / 12 h / 50 °C

2: 18.9 g / TsOH*H₂O / dimethylformamide / 17 h / 50 °C

3: 15.6 g / DIBAL-H / CH₂Cl₂; toluene / 4.5 h / -78 °C

4: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - -20 °C

5: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

6: 12.2 g / PPh₃ / CH₂Cl₂ / 1 h / -78 °C

7: 85 percent / PPh₃; Pd(OAc)2; Bu₃SnH / toluene / 0.5 h

With dmap; palladium diacetate; Amberlyst 15; tri-n-butyl-tin hydride; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 5: Dess-Martin oxidation / 6: Corey-Fuchs reaction;
DOI:10.1021/ja048320w

Reference yield:

: 377751-09-2
(2E,5R,6S)-6-[(4-methoxyphenyl)methoxy]-5-methyl-2-heptene-1,7-diol

: 640270-58-2
(1Z,3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene

Guidance literature:: Multi-step reaction with 4 steps

1: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - -20 °C

2: Dess-Martin periodinane / CH₂Cl₂ / 2 h / 0 °C

3: 12.2 g / PPh₃ / CH₂Cl₂ / 1 h / -78 °C

4: 85 percent / PPh₃; Pd(OAc)2; Bu₃SnH / toluene / 0.5 h

With dmap; palladium diacetate; tri-n-butyl-tin hydride; Dess-Martin periodane; triethylamine; triphenylphosphine; In dichloromethane; toluene; 2: Dess-Martin oxidation / 3: Corey-Fuchs reaction;
DOI:10.1021/ja048320w