Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl ester

Base Information

• Chemical Name: Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl ester
• CAS No.: 636564-12-0
• Molecular Formula: C₂₂H₂₈O₇S
• Molecular Weight: 436.526
• Mol file: 636564-12-0.mol

Synonyms:Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl ester

Chemical Property of Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl ester

There total 5 articles about Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl 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:

p-toluenesulfonyl chloride (98-59-9) + Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-hydroxy-butyl ester (636564-11-9) → Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl ester (636564-12-0)

Guidance literature:

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

DOI:10.1016/j.tetlet.2003.09.086

Reference yield:

(3S)-5-hydroxy-3-(2,5-dimethoxy-4-methylphenyl)pentyl acetate (321582-19-8) → Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl ester (636564-12-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: o-nitrophenyl selenocyanate; n-Bu₃P / tetrahydrofuran / 0.83 h / 20 °C

1.2: 48 percent / H₂O₂ / tetrahydrofuran / 10 h / 20 °C

2.1: O₃ / methanol

3.1: NaBH₄ / methanol / 1.5 h / -78 - 0 °C

4.1: Et₃N; 4-DMAP / CH₂Cl₂ / 16 h / 20 °C

With dmap; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; tributylphosphine; ozone; triethylamine; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1016/j.tetlet.2003.09.086

Reference yield:

3-(2,5-dimethoxy-4-methylphenyl)pentane-1,5-diol (321582-02-9) → Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-(toluene-4-sulfonyloxy)-butyl ester (636564-12-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 24 percent / immobilized lipase PS on diatomite / diethyl ether / 13 h / 20 °C

2.1: o-nitrophenyl selenocyanate; n-Bu₃P / tetrahydrofuran / 0.83 h / 20 °C

2.2: 48 percent / H₂O₂ / tetrahydrofuran / 10 h / 20 °C

3.1: O₃ / methanol

4.1: NaBH₄ / methanol / 1.5 h / -78 - 0 °C

5.1: Et₃N; 4-DMAP / CH₂Cl₂ / 16 h / 20 °C

With dmap; sodium tetrahydroborate; ortho-nitrophenyl selenocyanate; tributylphosphine; immobilized lipase PS on diatomite; ozone; triethylamine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane;

DOI:10.1016/j.tetlet.2003.09.086

upstream raw materials:

p-toluenesulfonyl chloride

Acetic acid (S)-3-(2,5-dimethoxy-4-methyl-phenyl)-4-hydroxy-butyl ester

3-(2,5-dimethoxy-4-methylphenyl)pentane-1,5-diol

(3S)-5-hydroxy-3-(2,5-dimethoxy-4-methylphenyl)pentyl acetate

Downstream raw materials:

(3S)-3-(2,5-Dimethoxy-4-methylphenyl)butan-2-ol