Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl ester
• CAS No.: 105311-37-3
• Molecular Formula: C₂₅H₄₄O₄SSi
• Molecular Weight: 468.773
• Mol file: 105311-37-3.mol

Synonyms:Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl ester

Chemical Property of Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl ester

There total 14 articles about Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl 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: 96.0%

t-butyldimethylsiyl triflate (69739-34-0) + Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-hydroxy-2,4,6-trimethyl-non-4-enyl ester (105311-36-2) → Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl ester (105311-37-3)

Guidance literature:

With triethylamine; In dichloromethane; at 0 ℃; for 1h;

DOI:10.1021/jo00375a060

Reference yield:

(E)-(2R,3R,6R)-2,4,6-Trimethyl-non-4-ene-1,3-diol (105311-35-1) → Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl ester (105311-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 76 percent / pyridine, DMAP / 0.5 h / 60 °C

2: 96 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; dmap; triethylamine; In dichloromethane;

DOI:10.1021/jo00375a060

Reference yield:

n-valeryl chloride (638-29-9) → Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-(tert-butyl-dimethyl-silanyloxy)-2,4,6-trimethyl-non-4-enyl ester (105311-37-3)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) n-BuLi / 1.) hexane, THF, -78 deg C, 2.) from -78 deg C to 0 deg C, 1 h

2: 1.) LDA / 1.) -78 deg C, 30 min, 2.) a) -78 deg C, 2 h, b) from -78 deg C to RT, 1 h

3: 80 percent / LAH / diethyl ether / 1 h / 0 °C

4: 1.) Me₂SO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 30 min, 2.) reflux, 48 h

5: DIBAL / hexane; CH₂Cl₂ / 1 h / -78 °C

6: Me₂SO, oxalyl chloride / CH₂Cl₂ / 0.5 h / -78 °C

7: 1.) TiCl₄, 2.) LAH / 1.) CH₂Cl₂, from -78 deg C to -50 deg C, 4 h, 2.) THF, ether, 9 deg C, 1 h

8: pyridine, DMAP / 0.5 h / 60 °C

9: 96 percent / triethylamine / CH₂Cl₂ / 1 h / 0 °C

With pyridine; dmap; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; titanium tetrachloride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; lithium diisopropyl amide; In diethyl ether; hexane; dichloromethane;

DOI:10.1021/jo00375a060

upstream raw materials:

t-butyldimethylsiyl triflate

Toluene-4-sulfonic acid (E)-(2R,3R,6R)-3-hydroxy-2,4,6-trimethyl-non-4-enyl ester

(E)-(2R,3R,6R)-2,4,6-Trimethyl-non-4-ene-1,3-diol

n-valeryl chloride

Downstream raw materials:

[(E)-(1R,4R)-1-((S)-2-Benzenesulfonyl-1-methyl-ethyl)-2,4-dimethyl-hept-2-enyloxy]-tert-butyl-dimethyl-silane