[2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester

Base Information

• Chemical Name: [2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester
• CAS No.: 440104-21-2
• Molecular Formula: C₃₀H₄₆O₇S₂Si
• Molecular Weight: 610.909
• Mol file: 440104-21-2.mol

Synonyms:[2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester

Chemical Property of [2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester

There total 6 articles about [2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-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: 67.0%

toluene-4-sulfonic acid 3-(6-benzenesulfonyl-4-methyl-hex-3-enyl)-3-methyl-oxiran-2-ylmethyl ester + t-butyldimethylsiyl triflate (69739-34-0) → [2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester (440104-21-2)

Guidance literature:

toluene-4-sulfonic acid 3-(6-benzenesulfonyl-4-methyl-hex-3-enyl)-3-methyl-oxiran-2-ylmethyl ester; With perchloric acid; In tetrahydrofuran; water; for 2h; Heating;

t-butyldimethylsiyl triflate; With 2,6-dimethylpyridine; In dichloromethane; at -20 ℃; for 1h; Further stages.;

DOI:10.1021/ol025872f

Reference yield:

[2E,6E]-9-benzenesulfonyl-3,7-dimethyl-nona-2,6-dien-1-ol (440104-18-7) → [2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester (440104-21-2)

Guidance literature:

Multi-step reaction with 3 steps

1.1: (+)-diisopropyl tartrate; titanium isopropoxide; tert-butyl hydroperoxide / CH₂Cl₂; decane / -20 °C

2.1: 95 percent / pyridine / CH₂Cl₂ / 48 h / -10 °C

3.1: perchloric acid / tetrahydrofuran; H₂O / 2 h / Heating

3.2: 67 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

With pyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; perchloric acid; L-(+)-diisopropyl tartrate; In tetrahydrofuran; decane; dichloromethane; water;

DOI:10.1021/ol025872f

Reference yield:

3-(6-benzenesulfonyl-4-methyl-hex-3-enyl)-3-methyl-oxiran-2-ylmethanol → [2R,3S,6E]-toluene-4-sulfonic acid-9-benzenesulfonyl-2-(t-butyldimethylsiloxy)-3-hydroxy-3,7-dimethyl-non-6-enyl ester (440104-21-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 95 percent / pyridine / CH₂Cl₂ / 48 h / -10 °C

2.1: perchloric acid / tetrahydrofuran; H₂O / 2 h / Heating

2.2: 67 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / -20 °C

With pyridine; perchloric acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/ol025872f

upstream raw materials:

t-butyldimethylsiyl triflate

[2E,6E]-9-benzenesulfonyl-3,7-dimethyl-nona-2,6-dien-1-ol

3,7-dimethyl-2E,6-octadien-1-yl acetate

(2E,6E)-8-bromo-3,7-dimethylocta-2,6-dienyl acetate

Downstream raw materials:

(2S)-4-(benzenesulfonyl)-2-[(2R,5S)-5-[(1R)-1-[(tert-butyldimethylsilyl)oxy]ethyl]-5-methyloxolan-2-yl]butan-2-ol

ionomycin

[2S,2(2R),5R,5(1S)]-5-[3-benzenesulfonyl-1-(trimethylsilyloxy)-1-methyl-propyl]-2-(1-(t-butyldimethylsiloxy)-ethyl)-2-methyl-tetrahydrofuran

benzoic acid 1-[2,5'-dimethyl-5'-(1-t-butyldimetylsilyloxy-ethyl)-octahydro-[2,2']bifuranyl-5-ylmethyl]-2,4-dimethyl-5-oxo-3-triisopropylsilyloxy-pentyl ester