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

Base Information

Chemical Name:(3S,4R,6E)-1,1-dibromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-1,6-octadiene
CAS No.:377751-03-6
Molecular Formula:C₃₃H₄₀Br₂O₃Si
Molecular Weight:672.572
Hs Code.:

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

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

There total 20 articles about (3S,4R,6E)-1,1-dibromo-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: 97.0%

: 58479-61-1
tert-butylchlorodiphenylsilane

: 377751-02-5
(2E,5R,6S)-8,8-dibromo-6-[(4-methoxyphenyl)methoxy]-5-methyl-2,7-octadien-1-ol

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

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; for 1.5h;
DOI:10.1021/ol016449u

Reference yield:

: 558-13-4
carbon tetrabromide

: (E)-(2S,3R)-7-(tert-Butyl-diphenyl-silanyloxy)-2-(4-methoxy-benzyloxy)-3-methyl-hept-5-enal

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

Guidance literature:: With triphenylphosphine; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1021/ja048320w

Reference yield:

: 377751-06-9
ethyl (2E,5R,6S)-6,7-(isopropylidene)dioxy-5-methyl-2-heptenoate

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

Guidance literature:: Multi-step reaction with 7 steps

1: DIBAL-H / CH₂Cl₂; toluene / 0.75 h / -78 °C

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

3: 18.9 g / TsOH*H₂O / dimethylformamide / 17 h / 50 °C

4: 15.6 g / DIBAL-H / CH₂Cl₂; toluene / 4.5 h / -78 °C

5: 73 percent / Et₃N; DMAP / CH₂Cl₂ / 2 h / -78 - -20 °C

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

7: 12.2 g / PPh₃ / CH₂Cl₂ / 1 h / -78 °C

With dmap; Amberlyst 15; diisobutylaluminium hydride; Dess-Martin periodane; toluene-4-sulfonic acid; triethylamine; triphenylphosphine; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene; 6: Dess-Martin oxidation / 7: Corey-Fuchs reaction;
DOI:10.1021/ja048320w