toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester

Base Information

Chemical Name:toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester
CAS No.:868548-00-9
Molecular Formula:C₂₁H₃₄O₃SSi
Molecular Weight:394.651
Hs Code.:

Synonyms:toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester

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Chemical Property of toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester

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Technology Process of toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester

There total 5 articles about toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl 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: 70.0%

: 868547-99-3
(R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 868548-00-9
toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester

Guidance literature:: (R)-4,4-dibromo-2-methyl-1-(toluene-4-sulfonyloxy)but-3-ene; With n-butyllithium; In tetrahydrofuran; at -78 ℃;

triisopropylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at 20 ℃; for 4h;
DOI:10.1021/ol051711a

Reference yield:

: 84341-89-9
(2S)-(+)-2-methyl-3-(toluene-4-sulfonyloxy)propionic acid methyl ester

: 868548-00-9
toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: DIBAL-H / toluene / 1.5 h / cooling

2.1: PPh₃ / CH₂Cl₂ / 0.17 h / cooling

2.2: 1.82 g / 2,6-lutidine / CH₂Cl₂ / 1 h / cooling

3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / cooling

3.2: 70 percent / tetrahydrofuran; hexane / 4 h / 20 °C

With n-butyllithium; diisobutylaluminium hydride; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane; toluene;
DOI:10.1016/j.tet.2006.05.019

Reference yield:

: 183293-41-6
(S)-O-p-toluenesulfonyl-3-hydroxy-2-methylpropanal

: 868548-00-9
toluene-4-sulfonic acid (R)-2-methyl-4-triisopropylsilanylbut-3-ynyl ester

Guidance literature:: Multi-step reaction with 2 steps

1.1: PPh₃ / CH₂Cl₂ / 0.17 h / cooling

1.2: 1.82 g / 2,6-lutidine / CH₂Cl₂ / 1 h / cooling

2.1: n-BuLi / tetrahydrofuran; hexane / 2 h / cooling

2.2: 70 percent / tetrahydrofuran; hexane / 4 h / 20 °C

With n-butyllithium; triphenylphosphine; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.tet.2006.05.019