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

Base Information

• Chemical Name: 1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)ethanone
• CAS No.: 1392302-24-7
• Molecular Formula: C₃₂H₃₈O₆
• Molecular Weight: 518.65
• Mol file: 1392302-24-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about 1-(2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)phenyl)-2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)ethanone 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: 87.0%

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 potassium tert-butylate; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

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:

2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)benzaldehyde (1309953-47-6) → 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:

Multi-step reaction with 4 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

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

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

DOI:10.1016/j.tetasy.2012.06.009

upstream raw materials:

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

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

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

Downstream raw materials:

methyl-2-(3,5-dihydroxy-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetyl)phenyl)acetate