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

Base Information

Chemical Name:(3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-6-octen-1-yne
CAS No.:773104-76-0
Molecular Formula:C₃₃H₃₉BrO₃Si
Molecular Weight:591.66
Hs Code.:

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

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

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

There total 8 articles about (3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-6-octen-1-yne 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: 93.0%

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

: 773104-76-0
(3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-6-octen-1-yne

Guidance literature:: With potassium tert-butylate; In tert-butyl alcohol; for 15h;
DOI:10.1021/ja048320w

Reference yield:

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

: 773104-76-0
(3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-6-octen-1-yne

Guidance literature:: Multi-step reaction with 8 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

8: 93 percent / t-BuOK / 2-methyl-propan-2-ol / 15 h

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

Reference yield:

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

: 773104-76-0
(3S,4R,6E)-1-bromo-8-(tert-butyldiphenylsilyloxy)-3-[(4-methoxyphenyl)methoxy]-4-methyl-6-octen-1-yne

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: 93 percent / t-BuOK / 2-methyl-propan-2-ol / 15 h

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