(3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol

Base Information

• Chemical Name: (3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol
• CAS No.: 1622982-75-5
• Molecular Formula: C₃₉H₅₆O₃Si
• Molecular Weight: 600.957
• Mol file: 1622982-75-5.mol

Synonyms:(3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol

Chemical Property of (3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol

There total 8 articles about (3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol 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:

(4R)-tridec-1-en-4-ol (99493-58-0) → (3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol (1622982-75-5)

Guidance literature:

Multi-step reaction with 8 steps

1: dmap; 1H-imidazole / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere

2: dimethyl sulfide borane / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

3: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 3 h / 20 °C / Inert atmosphere

4: dmap; triethylamine; N,O-dimethylhydroxylamine*hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 6 h / 20 °C / Inert atmosphere

5: vinyl magnesium bromide / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

6: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / tetrahydrofuran; toluene / 6 h / -78 °C / Inert atmosphere

7: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 12 h / 20 °C / Inert atmosphere

8: scandium tris(trifluoromethanesulfonate) / toluene / 0.25 h / -10 °C / Inert atmosphere

With 1H-imidazole; dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; vinyl magnesium bromide; N,O-dimethylhydroxylamine*hydrochloride; dimethyl sulfide borane; tetra-(n-butyl)ammonium iodide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; scandium tris(trifluoromethanesulfonate); (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1016/j.tet.2014.05.021

Reference yield:

(R)-tert-butyldiphenyl(tridec-1-en-4-yloxy)silane → (3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol (1622982-75-5)

Guidance literature:

Multi-step reaction with 7 steps

1: dimethyl sulfide borane / tetrahydrofuran / 2 h / 0 °C / Inert atmosphere

2: 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene / dichloromethane; water / 3 h / 20 °C / Inert atmosphere

3: dmap; triethylamine; N,O-dimethylhydroxylamine*hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 6 h / 20 °C / Inert atmosphere

4: vinyl magnesium bromide / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

5: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / tetrahydrofuran; toluene / 6 h / -78 °C / Inert atmosphere

6: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 12 h / 20 °C / Inert atmosphere

7: scandium tris(trifluoromethanesulfonate) / toluene / 0.25 h / -10 °C / Inert atmosphere

With dmap; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene; vinyl magnesium bromide; N,O-dimethylhydroxylamine*hydrochloride; dimethyl sulfide borane; tetra-(n-butyl)ammonium iodide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; scandium tris(trifluoromethanesulfonate); (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; water; toluene;

DOI:10.1016/j.tet.2014.05.021

Reference yield:

(R)-4-(tert-butyldiphenylsilyloxy)tridecanoic acid (1615198-65-6) → (3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol (1622982-75-5)

Guidance literature:

Multi-step reaction with 5 steps

1: dmap; triethylamine; N,O-dimethylhydroxylamine*hydrochloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 6 h / 20 °C / Inert atmosphere

2: vinyl magnesium bromide / tetrahydrofuran / 2 h / -78 °C / Inert atmosphere

3: (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; dimethyl sulfide borane / tetrahydrofuran; toluene / 6 h / -78 °C / Inert atmosphere

4: N-ethyl-N,N-diisopropylamine; tetra-(n-butyl)ammonium iodide / dichloromethane / 12 h / 20 °C / Inert atmosphere

5: scandium tris(trifluoromethanesulfonate) / toluene / 0.25 h / -10 °C / Inert atmosphere

With dmap; vinyl magnesium bromide; N,O-dimethylhydroxylamine*hydrochloride; dimethyl sulfide borane; tetra-(n-butyl)ammonium iodide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; scandium tris(trifluoromethanesulfonate); (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/j.tet.2014.05.021

upstream raw materials:

(4R)-tridec-1-en-4-ol

(R)-4-(tert-butyldiphenylsilyloxy)tridecan-1-ol

(R)-4-(tert-butyldiphenylsilyloxy)tridecanoic acid

(R)-4-(tert-butyldiphenylsilyloxy)-N-methoxy-N-methyltridecanamide

Downstream raw materials:

(3R,6R)-3-(4-methoxybenzyloxy)pentadec-1-en-6-ol