5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile

Base Information

Chemical Name:5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile
CAS No.:132047-95-1
Molecular Formula:C₃₈H₅₁NO₂Si₂
Molecular Weight:609.999
Hs Code.:

Synonyms:5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile

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Chemical Property of 5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile

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Technology Process of 5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile

There total 11 articles about 5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile 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

: 132047-95-1
5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile

Guidance literature:: Multi-step reaction with 4 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

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; TlOH; dicyclopentadienylzirconium hydrochloride; iodine; diisobutylaluminium hydride; 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

: 132047-95-1
5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile

Guidance literature:: Multi-step reaction with 5 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

With sodium periodate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; TlOH; carbon tetrabromide; dicyclopentadienylzirconium hydrochloride; iodine; diisobutylaluminium hydride; acetic acid; 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

: 132047-95-1
5(S)-(benzyloxy)-12<(tert-butyldiphenylsilyl)oxy>-7-(trimethylsilyl)undeca-6,8-dienenitrile

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: 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

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