[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile

Base Information

• Chemical Name: [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile
• CAS No.: 440104-12-1
• Molecular Formula: C₁₆H₂₃NO₂
• Molecular Weight: 261.364
• Mol file: 440104-12-1.mol

Synonyms:[3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile

Chemical Property of [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile

There total 9 articles about [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile 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: 95.0%

[2S,4R]-O-(4-toluene-sulfonate)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol (440104-11-0) + sodium cyanide (143-33-9,25596-52-5) → [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile (440104-12-1)

Guidance literature:

In dimethyl sulfoxide; at 85 ℃; for 5h;

DOI:10.1021/ol025872f

Reference yield:

methyl hydrogen meso-2,4-dimethylethylglutarate (7586-22-3,71372-08-2,82917-27-9,85646-66-8,92999-34-3,96612-17-8,100227-53-0,100227-54-1,114884-21-8) → [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile (440104-12-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 95 percent / H₂SO₄ / benzene / 18 h / Heating

2.1: α-chymotrypsin; NaOH / aq. phosphate buffer / 90 h / 20 °C / pH 7.5 - 7.8

3.1: 99 percent / B(OMe)3; BH₃*DMS / tetrahydrofuran / 42 h / 20 °C

4.1: 86 percent / imidasole / dimethylformamide / 18 h / 20 °C

5.1: 96 percent / DIBAL-H / toluene; heptane / 2 h / -78 °C

6.1: sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C

6.2: 91 percent / Bu₄NI / dimethylformamide; various solvent(s) / 18 h / 20 °C

7.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

8.1: 98 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 18 h / 20 °C

9.1: 95 percent / dimethylsulfoxide / 5 h / 85 °C

With 1H-imidazole; dmap; sodium hydroxide; Trimethyl borate; dimethylsulfide borane complex; sulfuric acid; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; α-chymotrypsin; In tetrahydrofuran; phosphate buffer; n-heptane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene; benzene;

DOI:10.1021/ol025872f

Reference yield:

[2R,4S]-2,4-dimethyl-pentanedioic acid monomethyl ester (96612-17-8) → [3S,5R]-6-(4-methoxy-benzyloxy)-3,5-dimethyl-hexanenitrile (440104-12-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 99 percent / B(OMe)3; BH₃*DMS / tetrahydrofuran / 42 h / 20 °C

2.1: 86 percent / imidasole / dimethylformamide / 18 h / 20 °C

3.1: 96 percent / DIBAL-H / toluene; heptane / 2 h / -78 °C

4.1: sodium hydride / dimethylformamide; various solvent(s) / 0.5 h / 0 °C

4.2: 91 percent / Bu₄NI / dimethylformamide; various solvent(s) / 18 h / 20 °C

5.1: 96 percent / tetrabutylammonium fluoride / tetrahydrofuran / 18 h / 20 °C

6.1: 98 percent / 4-dimethylaminopyridine; triethylamine / CH₂Cl₂ / 18 h / 20 °C

7.1: 95 percent / dimethylsulfoxide / 5 h / 85 °C

With 1H-imidazole; dmap; Trimethyl borate; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; triethylamine; In tetrahydrofuran; n-heptane; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ol025872f

upstream raw materials:

[2S,4R]-O-(4-toluene-sulfonate)-5-(4-methoxy-benzyloxy)-2,4-dimethyl-pentan-1-ol

sodium cyanide

methyl hydrogen meso-2,4-dimethylethylglutarate

[2R,4S]-2,4-dimethyl-pentanedioic acid monomethyl ester

Downstream raw materials:

[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R,14S,16S,18S]-benzoic acid 1-[5'-(1-TBDMS-ethyl)-2,5'-dimethyl-octahydro[2,2']bifuranyl-5-yl-methyl]-20-methoxycarbonyl-2,4,8,10,14,16,18-heptamethyl-11,13-dioxo-3-triisopropylsilyloxy-eicos-5-enyl ester

[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-(4-methoxy-benzyloxy)-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester

benzoic acid 3-hydroxy-1-[5'-(1-hydroxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-20-methoxycarbonyl-2,4,8,10,14,16,18-heptamethyl-11,13-dioxo-eicos-5-enyl ester

[1S,1(2S,5S,2'R,5'S,5'(1R)),2S,3R,4R,5E,8R,10R]-benzoic acid 1-[5'-(1-t-butyldimethylsilyloxy-ethyl)-2,5'-dimethyl-octahydro-[2,2']bifuranyl-5-yl-methyl]-11-hydroxy-2,4,8,10-tetramethyl-3-triisopropylsilyloxy-undec-5-enyl ester

Refernces