toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester

Base Information

Chemical Name:toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester
CAS No.:664994-92-7
Molecular Formula:C₂₄H₃₁NO₄SSi
Molecular Weight:457.666
Hs Code.:

Synonyms:toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester

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Chemical Property of toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester

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Technology Process of toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester

There total 1 articles about toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl 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:

: 772-03-2
2-vinylquinoline

: 18162-48-6
tert-butyldimethylsilyl chloride

: 98-59-9
p-toluenesulfonyl chloride

: 664994-92-7
toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester

Guidance literature:: 2-vinylquinoline; With potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium osmate(VI); In water; tert-butyl alcohol; at 0 ℃; for 6h;

p-toluenesulfonyl chloride; With pyridine; at -10 ℃; for 4h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In dichloromethane; at 20 ℃; for 5h;
DOI:10.1002/anie.200352755

Reference yield: 59.0%

: 664994-92-7
toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester

: (diphenyl)phosphine borane complex

: (1R)-2-[1-(tert-butyldimethylsilanyloxy)-2-(diphenylphosphanyl)ethyl]quinoline borane adduct

Guidance literature:: (diphenyl)phosphine borane complex; With n-butyllithium; In tetrahydrofuran; hexane; at -78 - 20 ℃;

toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester; In tetrahydrofuran; hexane; N,N-dimethyl-formamide; for 24h;
DOI:10.1002/anie.200352755

Reference yield:

: 664994-92-7
toluene-4-sulfonic acid (1R)-2-(tert-butyldimethylsilyloxy)-2-quinolin-2-ylethyl ester

: (1R)-2-[1-(tert-butyldiphenylsilyloxy)-2-(diphenylphosphanyl)ethyl]quinoline borane adduct

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-BuLi / tetrahydrofuran; hexane / -78 - 20 °C

1.2: 59 percent / hexane; tetrahydrofuran; dimethylformamide / 24 h

2.1: 99 percent / (n-Bu₄N)F / tetrahydrofuran / 4 h / 20 °C

3.1: 79 percent / imidazole / tetrahydrofuran / 4 h / 20 °C

With 1H-imidazole; n-butyllithium; tetrabutyl ammonium fluoride; In tetrahydrofuran; hexane;
DOI:10.1002/anie.200352755