Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-3-ynyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-3-ynyl ester
• CAS No.: 351412-68-5
• Molecular Formula: C₁₉H₂₈O₆SSi
• Molecular Weight: 412.579
• Mol file: 351412-68-5.mol

Synonyms:Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-3-ynyl ester

Chemical Property of Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-3-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-3-ynyl ester

There total 1 articles about Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-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: 99.0%

(2S)-2-[(1R)-3,3-dimethyl(2,4-dioxolanyl)]-4-trimethylsilylbut-3-yne-1,2-diol + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-3-ynyl ester (351412-68-5)

Guidance literature:

With pyridine; dmap; at 20 ℃; for 48h;

DOI:10.1021/ja003956i

Reference yield:

Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-3-ynyl ester (351412-68-5) → toluene-4-sulfonic acid 2,3-bis-(tert-butyl-dimethyl-silanyloxy)-6-[1-(tert-butyl-dimethyl-silanyloxy)-naphthalen-2-yl]-3-methyl-6-oxo-hex-4-ynyl ester

Guidance literature:

Multi-step reaction with 7 steps

1.1: 79 percent / LHMDS / tetrahydrofuran / 3 h / 0 °C

2.1: 98 percent / L-selectride / tetrahydrofuran / 3 h / 0 °C

3.1: TBAF; acetic acid / tetrahydrofuran / 1 h / 0 °C

3.2: HCl / tetrahydrofuran; H₂O / 24 h / 20 °C

4.1: 19 percent / pyridine / toluene / 12 h / 20 °C

5.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 12 h / 20 °C

6.1: CeCl₃ / tetrahydrofuran / 0.83 h / 20 °C

6.2: LHMDS / tetrahydrofuran / 0.5 h / -78 °C

6.3: 48 percent / tetrahydrofuran / 5 h / -78 °C

7.1: 81 percent / manganese (IV) oxide / CH₂Cl₂ / 12 h / 20 °C

With pyridine; 2,6-dimethylpyridine; manganese(IV) oxide; cerium(III) chloride; tetrabutyl ammonium fluoride; L-Selectride; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1021/ja003956i

Reference yield:

Toluene-4-sulfonic acid (S)-2-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-hydroxy-4-trimethylsilanyl-but-3-ynyl ester (351412-68-5) → [(2R,3R)-2,3-dihydroxy-3-methylpent-4-ynyl](4-methylphenyl)sulfonate (351412-72-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 79 percent / LHMDS / tetrahydrofuran / 3 h / 0 °C

2.1: 98 percent / L-selectride / tetrahydrofuran / 3 h / 0 °C

3.1: TBAF; acetic acid / tetrahydrofuran / 1 h / 0 °C

3.2: HCl / tetrahydrofuran; H₂O / 24 h / 20 °C

4.1: 19 percent / pyridine / toluene / 12 h / 20 °C

With pyridine; tetrabutyl ammonium fluoride; L-Selectride; acetic acid; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1021/ja003956i

upstream raw materials:

p-toluenesulfonyl chloride

Downstream raw materials:

[(2R,3R)-2,3-dihydroxy-3-methylpent-4-ynyl](4-methylphenyl)sulfonate

[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-3-methylpent-4-ynyl] (4-methylphenyl)sulfonate

[(2R,3R)-2,3-bis(tert-butyldimethylsilyloxy)-6-hydroxy-3-methyl-6-(1-(tert-butyldimethylsilyloxy)(2-naphthyl))hex-4-ynyl] (4-methylphenyl)sulfonate