7(S)-(benzyloxy)-14-<(tert-butyldiphenylsilyl)oxy>-2-methyl-9-(trimethylsilyl)tetradeca-2,8,10-trienal

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Chemical Name:7(S)-(benzyloxy)-14-<(tert-butyldiphenylsilyl)oxy>-2-methyl-9-(trimethylsilyl)tetradeca-2,8,10-trienal
CAS No.:132048-01-2
Molecular Formula:C₄₁H₅₆O₃Si₂
Molecular Weight:653.065
Hs Code.:

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

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

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

There total 14 articles about 7(S)-(benzyloxy)-14-<(tert-butyldiphenylsilyl)oxy>-2-methyl-9-(trimethylsilyl)tetradeca-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

: 132048-01-2
7(S)-(benzyloxy)-14-<(tert-butyldiphenylsilyl)oxy>-2-methyl-9-(trimethylsilyl)tetradeca-2,8,10-trienal

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) n-BuLi / 1.) THF, -78 deg C

2: 1.) diisobutylaluminum hydride, 2.) I₂ / 1.) hexane, Et₂O

3: 74 percent / TlOH, Pd(PPh₃)4 / dioxane / 23 °C

4: 1.) Cp₂Zr*HCl, 3.) I₂

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

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

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; TlOH; oxalyl dichloride; dicyclopentadienylzirconium hydrochloride; oxonium; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; In 1,4-dioxane;
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

: 132048-01-2
7(S)-(benzyloxy)-14-<(tert-butyldiphenylsilyl)oxy>-2-methyl-9-(trimethylsilyl)tetradeca-2,8,10-trienal

Guidance literature:: Multi-step reaction with 7 steps

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

2: 1.) n-BuLi / 1.) THF, -78 deg C

3: 1.) diisobutylaluminum hydride, 2.) I₂ / 1.) hexane, Et₂O

4: 74 percent / TlOH, Pd(PPh₃)4 / dioxane / 23 °C

5: 1.) Cp₂Zr*HCl, 3.) I₂

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

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

With sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; TlOH; oxalyl dichloride; carbon tetrabromide; dicyclopentadienylzirconium hydrochloride; oxonium; iodine; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triphenylphosphine; In 1,4-dioxane;
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

: 132048-01-2
7(S)-(benzyloxy)-14-<(tert-butyldiphenylsilyl)oxy>-2-methyl-9-(trimethylsilyl)tetradeca-2,8,10-trienal

Guidance literature:: Multi-step reaction with 11 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: 1) N-BuLi / 1a) THF, hexane, -78 deg C, 1h, 1b) 23 deg C, 1h, 2a) -78 deg C, 1h, 2b) 23 deg C, 4.5h

6: 1) 1M DIBAL-H, 2) I₂ / 1a) Et₂O, hexane, 0 deg C, 15 min, 1b) 23 deg C, 19h, 2) THF, 23 deg C, 9.5h

7: 74 percent / aq TlOH / Pd(PPh₃)4 / dioxane / 0.08 h

9: 1) 1M DIBAL / 1) Et₂O, hexane, 23 deg C, 2) CH₂Cl₂, 23 deg C

10: DIBAL-H / diethyl ether; hexane / 1) -78 deg C, 1.5h, 2) -78 to 23 deg C

11: 1) (COCl)2, DMSO, 2) NEt₃ / 1) CH₂Cl₂, -78 deg C, 15 min, 2) -78 to 0 deg C, 2h

With sodium periodate; n-butyllithium; TlOH; oxalyl dichloride; iodine; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; triphenylphosphine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water;
DOI:10.1021/jo00003a049