4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane

Base Information

Chemical Name:4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane
CAS No.:925231-61-4
Molecular Formula:C₃₅H₅₄O₄Si₂
Molecular Weight:594.982
Hs Code.:

4-(<i>tert</i>-butyl-dimethyl-silanyloxymethyl)-5-[6-(<i>tert</i>-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane

Synonyms:4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane

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Chemical Property of 4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane

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Technology Process of 4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane

There total 3 articles about 4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane 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: 99.0%

: tert-butyl-[5-(2-iodo-vinyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy]-dimethyl-silane

: 925231-60-3
C₂₁H₂₉BO₃Si

: 925231-61-4
4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: With thallium (I) ethoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; water; at 20 ℃; for 2h;
DOI:10.1002/anie.200603363

Reference yield:

: 95514-03-7
(S)-3-(tert-butyl-diphenyl-silanyloxy)-2-methyl-propionic acid methyl ester

: 925231-61-4
4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 6 steps

1.1: 97 percent / LiBH₄ / tetrahydrofuran; diethyl ether / 24 h / 20 °C

2.1: 90 percent / Et₃N; SO₃; pyridine / CH₂Cl₂; dimethylsulfoxide / 1 h / 20 °C

3.1: Zn; Ph₃P / CH₂Cl₂ / 0.33 h / cooling

3.2: CH₂Cl₂ / 4 h / 20 °C

4.1: 5.61 g / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: BHBr₂*SMe₂ / CH₂Cl₂ / 2 h / 20 °C

5.2: 80 percent / H₂O / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

6.1: 99 percent / TlOEt / Pd(Ph₃P)4 / tetrahydrofuran; H₂O / 2 h / 20 °C

With pyridine; lithium borohydride; n-butyllithium; dibromoborane dimethylsulfide; sulfur trioxide; thallium (I) ethoxide; triethylamine; triphenylphosphine; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; water; dimethyl sulfoxide; 3.2: Corey-Fuchs homologation / 6.1: Suzuki coupling;
DOI:10.1002/anie.200603363

Reference yield:

: 194610-23-6
(R)-tert-butyl((4,4-dibromo-2-methylbut-3-en-1-yl)oxy)diphenylsilane

: 925231-61-4
4-(tert-butyl-dimethyl-silanyloxymethyl)-5-[6-(tert-butyl-diphenyl-silanyloxy)-5-methyl-hexa-1,3-dienyl]-2,2-dimethyl-[1,3]dioxolane

Guidance literature:: Multi-step reaction with 3 steps

1.1: 5.61 g / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

2.1: BHBr₂*SMe₂ / CH₂Cl₂ / 2 h / 20 °C

2.2: 80 percent / H₂O / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

3.1: 99 percent / TlOEt / Pd(Ph₃P)4 / tetrahydrofuran; H₂O / 2 h / 20 °C

With n-butyllithium; dibromoborane dimethylsulfide; thallium (I) ethoxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; hexane; dichloromethane; water; 3.1: Suzuki coupling;
DOI:10.1002/anie.200603363