toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester

Base Information

Chemical Name:toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester
CAS No.:866412-23-9
Molecular Formula:C₂₃H₃₂O₄SSi
Molecular Weight:432.656
Hs Code.:

toluene-4-sulfonic acid 4-[1-(<i>tert</i>-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester

Synonyms:toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester

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Chemical Property of toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester

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Technology Process of toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester

There total 2 articles about toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester 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: 87.0%

: 18162-48-6
tert-butyldimethylsilyl chloride

: 477284-07-4
Toluene-4-sulfonic acid 4-((S)-1-hydroxy-but-3-enyl)-phenyl ester

: 866412-23-9
toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester

Guidance literature:: With 1H-imidazole; In dichloromethane; at 0 ℃; for 4h;
DOI:10.1016/j.tetlet.2005.07.162

Reference yield:

: 80459-48-9
4-tosyloxybenzaldehyde

: 866412-23-9
toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 73 percent / (S)-BINOL; Ti(OiPr)4; 4 Angstroem MS / CH₂Cl₂ / 70 h / -20 °C

2: 87 percent / imidazole / CH₂Cl₂ / 4 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; 4 Angstroem MS; (S)-[1,1']-binaphthalenyl-2,2'-diol; In dichloromethane; 1: Keck allylation;
DOI:10.1016/j.tetlet.2005.07.162

Reference yield:

: 866412-23-9
toluene-4-sulfonic acid 4-[1-(tert-butyl-dimethyl-silanyloxy)-but-3-enyl]-phenyl ester

: (-)-4-O-methylcentrolobol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 85 percent / Mg / methanol / 3 h / 20 °C

2.1: 73 percent / K₂CO₃ / acetone / 4 h / Heating

3.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

3.2: TPP / CH₂Cl₂

4.1: CH₂Cl₂ / 2 h / 20 °C

5.1: 81 percent / Mg / 3 h / 20 °C

6.1: 76 percent / LAH / tetrahydrofuran / 3 h / 0 - 20 °C

7.1: 80 percent / IBX / dimethylsulfoxide / 4 h / 20 °C

8.1: 81 percent / Ba(OH)2*8H₂O / tetrahydrofuran; H₂O / 5 h / 20 °C

9.1: 80 percent / HF*Py / tetrahydrofuran / 4 h / Heating

10.1: H₂ / Pd/C / ethanol / 760 Torr

With barium dihydroxide; lithium aluminium tetrahydride; hydrogen; potassium carbonate; pyridine hydrogenfluoride; ozone; magnesium; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; palladium on activated charcoal; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; dimethyl sulfoxide; acetone; 4.1: Wittig olefination / 9.1: intramolecular oxy-Michael addition;
DOI:10.1016/j.tetlet.2005.07.162