Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentyl ester
• CAS No.: 899798-70-0
• Molecular Formula: C₃₁H₄₂O₆SSi
• Molecular Weight: 570.822
• Mol file: 899798-70-0.mol

Synonyms:Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentyl ester

Chemical Property of Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentyl ester

There total 2 articles about Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-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: 87.0%

(2S,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentan-1-ol (899798-69-7) + p-toluenesulfonyl chloride (98-59-9) → Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentyl ester (899798-70-0)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/ol060669w

Reference yield:

3-(tert-butyldiphenylsilyloxy)-1-propanal (112897-03-7) → Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentyl ester (899798-70-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: nBu₂BOTf; N,N-diisopropylethylamine / CH₂Cl₂ / 0.5 h / -5 °C

1.2: 94 percent / CH₂Cl₂ / 16 h / -78 °C

2.1: 91 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 4 h / Heating

3.1: 94 percent / lithium aluminum hydride / diethyl ether / 2 h / 0 °C

4.1: 87 percent / triethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 16 h / 20 °C

With dmap; lithium aluminium tetrahydride; di-n-butylboryl trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; In diethyl ether; dichloromethane;

DOI:10.1021/ol060669w

Reference yield:

Toluene-4-sulfonic acid (2S,3S)-5-(tert-butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentyl ester (899798-70-0) → C48H86O6Si3 (899798-82-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / dimethylsulfoxide / 2 h / 80 °C

2: diisobutylaluminum hydride / tetrahydrofuran; hexane / -78 - 20 °C

3: 75 percent Turnov_. / sodium hexamethyldisilazide / 1,2-dimethoxy-ethane; hexamethylphosphoric acid triamide; tetrahydrofuran / 2 h / -78 °C

With sodium hexamethyldisilazane; diisobutylaluminium hydride; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; 1,2-dimethoxyethane; hexane; dimethyl sulfoxide; 3: Julia-Kocienski olefination;

DOI:10.1021/ol060669w

upstream raw materials:

(2S,3S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-methoxymethoxy-2-methyl-pentan-1-ol

p-toluenesulfonyl chloride

3-(tert-butyldiphenylsilyloxy)-1-propanal

Downstream raw materials:

C₄₈H₈₆O₆Si₃