7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal

Base Information

Chemical Name:7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal
CAS No.:132048-02-3
Molecular Formula:C₃₈H₄₇BrO₃Si
Molecular Weight:659.779
Hs Code.:

Synonyms:7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal

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Chemical Property of 7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal

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Technology Process of 7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal

There total 14 articles about 7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal 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:

: 112505-92-7
(S)-3-(benzyloxy)-1,1-dibromo-hexa-1,5-diene

: 132048-02-3
7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal

Guidance literature:: Multi-step reaction with 4 steps

1: 65 percent / TlOH / Pd(PPh₃)4 / tetrahydrofuran / 23 °C

2: 1.) Cp₂Zr*HCl, 3.) I₂

3: 1.) diisobutylaluminum hydride, 2.) H₃O⁽¹⁺⁾ / 1.) (C₂H₅)2O, 25 deg C, 2.) CH₂Cl₂, 25 deg C

4: 1.) diisobutylaluminum hydride, 2.)DMSO, (COCl)2 / 1.) (C₂H₅)2O, -78 deg C

With TlOH; oxalyl dichloride; dicyclopentadienylzirconium hydrochloride; oxonium; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;
DOI:10.1021/jo00238a049

Reference yield:

: 87604-53-3
(R)-4-((S)-1-(benzyloxy)but-3-ene-1-yl)-2,2-dimethyl-1,3-dioxypentane

: 132048-02-3
7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal

Guidance literature:: Multi-step reaction with 5 steps

1: 1.) HOAc, 2.) NaIO₄, 3.) CBr₄, PPh₃

2: 65 percent / TlOH / Pd(PPh₃)4 / tetrahydrofuran / 23 °C

3: 1.) Cp₂Zr*HCl, 3.) I₂

4: 1.) diisobutylaluminum hydride, 2.) H₃O⁽¹⁺⁾ / 1.) (C₂H₅)2O, 25 deg C, 2.) CH₂Cl₂, 25 deg C

5: 1.) diisobutylaluminum hydride, 2.)DMSO, (COCl)2 / 1.) (C₂H₅)2O, -78 deg C

With sodium periodate; TlOH; oxalyl dichloride; carbon tetrabromide; dicyclopentadienylzirconium hydrochloride; oxonium; iodine; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran;
DOI:10.1021/jo00238a049

Reference yield:

: 79364-35-5
(S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

: 132048-02-3
7(S)-(benzyloxy)-9-bromo-14-<(tert-butyldiphenylsilyl)oxy>2-methyltetradeca-2,8,10-trienal

Guidance literature:: Multi-step reaction with 8 steps

1: 1) NaH / 1) DMF, 0 deg C, 15 min, 2) 23 deg C, 2h

2: 60percent HOAc / tetrahydrofuran / 5 h / 50 °C

3: NaIO₄ / tetrahydrofuran; H₂O / 1) 0 deg C, 30 min, 2) 23 deg C, 1h

4: PPh₃ / CH₂Cl₂ / 0 °C

5: 2) 10percent aq. TlOH / 1) Pd(PPh₃)4 / 1) THF, 23 deg C, 0.5h, 2) THF, 23 deg C, 10-15 min

7: 1.0M DIBAL / diethyl ether; hexane / 4 h / 23 °C

8: 1) sec-BuLi / 1) THF, cyclohexane, -78 deg C, 30 min, 2) -20 deg C, 4.5h

With sodium periodate; TlOH; sec.-butyllithium; sodium hydride; diisobutylaluminium hydride; acetic acid; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water;
DOI:10.1021/jo00003a049