2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-enyl ester

Base Information

• Chemical Name: 2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-enyl ester
• CAS No.: 155300-06-4
• Molecular Formula: C₁₇H₂₆O₄S
• Molecular Weight: 326.457
• Mol file: 155300-06-4.mol

Synonyms:2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-enyl ester

Chemical Property of 2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-enyl ester

There total 2 articles about 2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-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: 94.0%

2-mesitylenesulphonyl chloride (773-64-8) + (2S,3S,4S)-2,4-Dimethylhex-5-ene-1,3-diol (155417-64-4) → 2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-enyl ester (155300-06-4)

Guidance literature:

With triethylamine; In dichloromethane;

DOI:10.1016/S0040-4039(00)76542-7

Reference yield:

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene (106357-24-8) → 2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-enyl ester (155300-06-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / nBu₄NF / tetrahydrofuran

2: 94 percent / Et₃N / CH₂Cl₂

With tetrabutyl ammonium fluoride; triethylamine; In tetrahydrofuran; dichloromethane;

DOI:10.1016/S0040-4039(00)76542-7

Reference yield:

2,4,6-Trimethyl-benzenesulfonic acid (2S,3S,4S)-3-hydroxy-2,4-dimethyl-hex-5-enyl ester (155300-06-4) → (2R,3S)-5-Benzenesulfonyl-3-methyl-2-((S)-1-methyl-allyl)-tetrahydro-furan (213262-40-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 97 percent / dimethylsulfoxide / 60 °C

2: 94 percent / DIBAL-H / toluene / -78 °C

3: 93 percent / CaCl₂ / CH₂Cl₂

With diisobutylaluminium hydride; calcium chloride; In dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/S0040-4039(00)76542-7

upstream raw materials:

2-mesitylenesulphonyl chloride

(2S,3S,4S)-2,4-Dimethylhex-5-ene-1,3-diol

(3S,4S,5S)-6-(tert-butyldiphenylsiloxy)-4-hydroxy-3,5-dimethylhexan-1-ene

Downstream raw materials:

(2R,3S)-5-Benzenesulfonyl-3-methyl-2-((S)-1-methyl-allyl)-tetrahydro-furan