Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester
CAS No.:214773-37-2
Molecular Formula:C₂₇H₄₂O₅SSi
Molecular Weight:506.779
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester

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Chemical Property of Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester

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Technology Process of Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester

There total 8 articles about Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl 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: 84.0%

: 98-59-9
p-toluenesulfonyl chloride

: 214773-33-8
(2S,3S)-2-Benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-heptan-3-ol

: 214773-37-2
Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester

Guidance literature:: With dmap; In dichloromethane; for 12h; Ambient temperature;
DOI:10.1002/jhet.5570350414

Reference yield:

: 100-39-0
benzyl bromide

: 214773-37-2
Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, from 0 deg C to RT, 15 min, 2.) THF, RT, 3 h

2: 88 percent / NaBH₄ / ethanol / 2 h / Heating

3: 74 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 1 h / Heating

4: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

With dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; In ethanol; dichloromethane; toluene;
DOI:10.1002/jhet.5570350414

Reference yield:

: 18162-48-6
tert-butyldimethylsilyl chloride

: 214773-37-2
Toluene-4-sulfonic acid (S)-1-((S)-1-benzyloxy-ethyl)-5-(tert-butyl-dimethyl-silanyloxy)-pentyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 84 percent / imidazole / CH₂Cl₂ / 14 h / Ambient temperature

2: 90 percent / m-CPBA / CH₂Cl₂ / 2 h / 0 °C

3: 1.) NaH, 2.) tetrabutylammonium iodide / 1.) THF, from 0 deg C to RT, 15 min, 2.) THF, RT, 3 h

4: 88 percent / NaBH₄ / ethanol / 2 h / Heating

5: 74 percent / tributyltin hydride, 2,2'-azobisisobutyronitrile / toluene / 1 h / Heating

6: 84 percent / 4-dimethylaminopyridine / CH₂Cl₂ / 12 h / Ambient temperature

With 1H-imidazole; dmap; sodium tetrahydroborate; 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; tetra-(n-butyl)ammonium iodide; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In ethanol; dichloromethane; toluene;
DOI:10.1002/jhet.5570350414