5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal

Base Information

Chemical Name:5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal
CAS No.:808739-75-5
Molecular Formula:C₂₉H₄₂O₆SSi
Molecular Weight:546.8
Hs Code.:

Synonyms:5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal

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Chemical Property of 5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal

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Technology Process of 5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal

There total 4 articles about 5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal 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: 80.0%

: 808739-74-4
2-(2-{2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}-2-[(4-methylphenyl)sulfonyl]pent-4-yl)-2-methyl-1,3-dioxolane

: 808739-75-5
5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal

Guidance literature:: 2-(2-{2-[4-(tert-butyldimethylsilyloxy)phenyl]ethyl}-2-[(4-methylphenyl)sulfonyl]pent-4-yl)-2-methyl-1,3-dioxolane; With ozone; In dichloromethane; at -78 ℃; for 0.166667h;

With acetic acid; zinc; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1055/s-2004-831240

Reference yield:

: 147974-20-7
3-[4-(tert-butyl-dimethyl-silanyloxy)phenyl]propionaldehyde

: 808739-75-5
5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal

Guidance literature:: Multi-step reaction with 5 steps

1.1: 80 percent / K₂CO₃; 18-crown-6 / toluene / 2 h / Heating

2.1: 90 percent / AcOH / ethanol / 48 h / 20 °C

3.1: 80 percent / p-TsOH / toluene / 2.5 h / Heating

4.1: t-BuLi / hexane; tetrahydrofuran / 0.33 h / 0 °C

4.2: 75 percent / hexane; tetrahydrofuran / 12 h / 20 °C

5.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

5.2: 80 percent / AcOH; Zn / CH₂Cl₂ / 2 h / 20 °C

With 18-crown-6 ether; tert.-butyl lithium; potassium carbonate; toluene-4-sulfonic acid; ozone; acetic acid; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene; 1.1: Wittig reaction;
DOI:10.1055/s-2004-831240

Reference yield:

: 808739-71-1
(3E)-6-[4-(tert-butyldimethylsilyloxy)phenyl]hex-3-en-2-one

: 808739-75-5
5-[4-(tert-butyldimethylsilyloxy)phenyl]-3-(2-methyl-1,3-dioxolan-2-ylmethyl)-3-[(4-methylphenyl)sulfonyl]pentanal

Guidance literature:: Multi-step reaction with 4 steps

1.1: 90 percent / AcOH / ethanol / 48 h / 20 °C

2.1: 80 percent / p-TsOH / toluene / 2.5 h / Heating

3.1: t-BuLi / hexane; tetrahydrofuran / 0.33 h / 0 °C

3.2: 75 percent / hexane; tetrahydrofuran / 12 h / 20 °C

4.1: O₃ / CH₂Cl₂ / 0.17 h / -78 °C

4.2: 80 percent / AcOH; Zn / CH₂Cl₂ / 2 h / 20 °C

With tert.-butyl lithium; toluene-4-sulfonic acid; ozone; acetic acid; In tetrahydrofuran; ethanol; hexane; dichloromethane; toluene;
DOI:10.1055/s-2004-831240