((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol

Base Information

Chemical Name:((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol
CAS No.:925231-62-5
Molecular Formula:C₂₉H₄₀O₄Si
Molecular Weight:480.72
Hs Code.:

Synonyms:((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol

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Chemical Property of ((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol

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Technology Process of ((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol

There total 13 articles about ((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol 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: 86.0%

: (R,E)-tert-butyl(4-iodo-2-methylbut-3-enyloxy)diphenylsilane

: 1446318-82-6
(4R,5R)-2,2-dimethyl-5-((E)-2-(tributylstannyl)vinyl)-1,3-dioxolan-4-ylmethanol

: 925231-62-5
((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol

Guidance literature:: With copper(I) chloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; lithium chloride; In dimethyl sulfoxide; at 20 - 60 ℃; for 2h; Inert atmosphere;

Reference yield: 75.0%

: (2R,7R,8R)-1-tert-butyldiphenylsilyloxy-7,8-O-isopropylidene-2-methyl-9-(triethylsilyloxy)-3,5-nonadiene

: 925231-62-5
((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol

: (2R,3R,4Z,6E,7R)-9-tert-butyldiphenylsilyloxy-2,3-O-isopropylidene-8-methylnona-4,6-dien-1-ol

Guidance literature:: With pyridinium p-toluenesulfonate; In ethanol; dichloromethane; at 0 - 20 ℃; Inert atmosphere;
DOI:10.1021/acs.joc.7b01973

Reference yield:

: 92817-88-4
(2S)-3-{[tert-butyl(diphenyl)silyl]oxy}-2-methylpropanal

: 925231-62-5
((4R,5R)-5-((R,1E,3E)-6-(tert-butyldiphenylsilyloxy)-5-methylhexa-1,3-dienyl)-2,2-dinethyl-1,3-dioxolan-4-yl)methanol

Guidance literature:: Multi-step reaction with 5 steps

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

1.2: CH₂Cl₂ / 4 h / 20 °C

2.1: 5.61 g / n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C

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

3.2: 80 percent / H₂O / CH₂Cl₂; diethyl ether / 0.5 h / 20 °C

4.1: 99 percent / TlOEt / Pd(Ph₃P)4 / tetrahydrofuran; H₂O / 2 h / 20 °C

5.1: 80 percent / pyridinium p-toluenesulfonate / ethanol / 12 h / 20 °C

With n-butyllithium; dibromoborane dimethylsulfide; thallium (I) ethoxide; pyridinium p-toluenesulfonate; triphenylphosphine; zinc; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; ethanol; hexane; dichloromethane; water; 1.2: Corey-Fuchs homologation / 4.1: Suzuki coupling;
DOI:10.1002/anie.200603363