[(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane
CAS No.:927396-57-4
Molecular Formula:C₂₆H₄₅BrO₃Si
Molecular Weight:513.631
Hs Code.:

Synonyms:[(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane

There total 7 articles about [(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane 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%

: 927396-56-3
(E)-(3R,6S,9S)-9-(tert-Butyl-dimethyl-silanyloxy)-3-(4-methoxy-benzyloxy)-6,8-dimethyl-dec-7-en-1-ol

: 927396-57-4
[(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 1h;
DOI:10.1021/ol062957y

Reference yield:

: 927396-58-5
(S)-4-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methylbutyraldehyde

: 927396-57-4
[(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 5 steps

1: 0.750 g / Ba(OH)2 / tetrahydrofuran; H₂O / 0.5 h / 20 °C

2: (R)-CBS; catecholborane / toluene / 12 h / -78 °C

3: 86 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

4: 98 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / 0 °C

5: 97 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; barium dihydroxide; carbon tetrabromide; diisobutylaluminium hydride; triphenylphosphine; (R)-(+)-2-methyl-CBS-oxazaborolidine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; dichloromethane; water; toluene;
DOI:10.1021/ol062957y

Reference yield:

: 927396-54-1
(S)-4-[(4R)-2-(4-methoxyphenyl)-[1,3]dioxan-4-yl]-2-methylbutan-1-ol

: 927396-57-4
[(E)-(1S,4S,7R)-9-bromo-7-(4-methoxy-benzyloxy)-1,2,4-trimethyl-non-2-enyloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 6 steps

1: oxalyl chloride; dimethyl sulfoxide; triethylamine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

2: 0.750 g / Ba(OH)2 / tetrahydrofuran; H₂O / 0.5 h / 20 °C

3: (R)-CBS; catecholborane / toluene / 12 h / -78 °C

4: 86 percent / 2,6-lutidine / CH₂Cl₂ / 2 h / 0 °C

5: 98 percent / diisobutylaluminum hydride / CH₂Cl₂; hexane / 0.5 h / 0 °C

6: 97 percent / triphenylphosphine; carbon tetrabromide / CH₂Cl₂ / 1 h / 20 °C

With 2,6-dimethylpyridine; barium dihydroxide; oxalyl dichloride; carbon tetrabromide; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; triphenylphosphine; (R)-(+)-2-methyl-CBS-oxazaborolidine; benzo[1,3,2]dioxaborole; In tetrahydrofuran; hexane; dichloromethane; water; toluene; 1: Swern oxidation;
DOI:10.1021/ol062957y