(R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one

Base Information

• Chemical Name: (R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one
• CAS No.: 1392302-22-5
• Molecular Formula: C₃₈H₅₂O₆Si
• Molecular Weight: 632.913
• Mol file: 1392302-22-5.mol

Synonyms:(R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one

Chemical Property of (R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one

There total 1 articles about (R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one 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:

2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)benzaldehyde (1309953-47-6) → (R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one (1392302-22-5)

Guidance literature:

Multi-step reaction with 3 steps

1: tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

2: tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide / dichloromethane / 2 h / 20 °C / Inert atmosphere; Molecular sieve

3: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / dichloromethane / 2 h / 45 °C / Inert atmosphere

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrapropylammonium perruthennate; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.tetasy.2012.06.009

Reference yield: 34.0%

(R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one (1392302-22-5) → 1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-2-((2S,6R)-6-methyltetrahydro-2H-pyran-2-yl)ethanone (1392302-23-6) + 1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)ethanone (1392302-24-7)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 15h; optical yield given as %de; Inert atmosphere;

DOI:10.1016/j.tetasy.2012.06.009

Reference yield:

(R,E)-1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-7-(triethylsilyloxy)oct-2-en-1-one (1392302-22-5) → C30H32O6

Guidance literature:

Multi-step reaction with 2 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 15 h / 20 °C / Inert atmosphere

2: Jones reagent / acetone / 0.5 h / 0 °C / Inert atmosphere

With Jones reagent; tetrabutyl ammonium fluoride; In tetrahydrofuran; acetone; 1: oxy-Michael reaction;

DOI:10.1016/j.tetasy.2012.06.009

upstream raw materials:

2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)benzaldehyde

Downstream raw materials:

methyl 2-(3,5-bis(benzyloxy)-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)ethanoyl)phenyl)ethanoate

1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-2-((2S,6R)-6-methyltetrahydro-2H-pyran-2-yl)ethanone

1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)ethanone