2-Hexenoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, (2E,4R)-

Base Information

• Chemical Name: 2-Hexenoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, (2E,4R)-
• CAS No.: 669000-37-7
• Molecular Formula: C20H32O6SSi
• Molecular Weight: 428.622
• Mol file: 669000-37-7.mol

Synonyms:

Chemical Property of 2-Hexenoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, (2E,4R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Hexenoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, (2E,4R)-

There total 2 articles about 2-Hexenoic acid, 4-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-6-[[(4-methylphenyl)sulfonyl]oxy]-, methyl ester, (2E,4R)- 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: 99.0%

p-toluenesulfonyl chloride (98-59-9) + methyl (2E,4R)-4-<<(tert-butyl)dimethylsilyl>oxy>-6-hydroxyhex-2-eneoate (157918-29-1) → (E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyloxy)-hex-2-enoic acid methyl ester (669000-37-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃;

DOI:10.1021/ol0363366

Reference yield:

(R)-3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one (669000-31-1) → (E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyloxy)-hex-2-enoic acid methyl ester (669000-37-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

1.2: tetrahydrofuran; hexane / -78 °C

1.3: 85 percent / DIBAL / tetrahydrofuran; hexane; toluene

2.1: 99 percent / triethylamine; 4-(dimethylamino)pyridine / CH₂Cl₂ / 0 - 20 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; hexane; dichloromethane;

DOI:10.1021/ol0363366

Reference yield: 96.0%

(E)-(R)-4-(tert-Butyl-dimethyl-silanyloxy)-6-(toluene-4-sulfonyloxy)-hex-2-enoic acid methyl ester (669000-37-7) → (3R,4E)-3-tert-butyldimethylsilyloxy-6-hydroxy-4-hexenyl 4-methylbenzenesulfonate (669000-32-2)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -78 - -40 ℃;

DOI:10.1021/ol0363366

upstream raw materials:

p-toluenesulfonyl chloride

methyl (2E,4R)-4-<<(tert-butyl)dimethylsilyl>oxy>-6-hydroxyhex-2-eneoate

(R)-3-(tert-butyldimethylsilyloxy)dihydrofuran-2(3H)-one

Downstream raw materials:

(3R,4E)-3-tert-butyldimethylsilyloxy-6-hydroxy-4-hexenyl 4-methylbenzenesulfonate

(R)-3-Benzenesulfonyl-6-((E)-3-hydroxy-propenyl)-tetrahydro-pyran-2-one

(E)-(R)-2-Benzenesulfonyl-5,8-dihydroxy-oct-6-enoic acid methyl ester

ethyl (E)-3-(2R)-6-oxo-5-phenylsulfonyltetrahydro-2H-pyran-2-yl-2-propenyl carbonate