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

Base Information

• Chemical Name: methyl-2-(3,5-dihydroxy-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetyl)phenyl)acetate
• CAS No.: 1263694-22-9
• Molecular Formula: C₁₇H₂₂O₆
• Molecular Weight: 322.358
• Mol file: 1263694-22-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 27 articles about methyl-2-(3,5-dihydroxy-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetyl)phenyl)acetate 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: 91.0%

methyl 2-(3,5-dimethoxy-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetyl)phenyl)acetate → methyl-2-(3,5-dihydroxy-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetyl)phenyl)acetate (1263694-22-9)

Guidance literature:

With 3,5-dihydroxyphenol; iodine; tetra-(n-butyl)ammonium iodide; aluminium; In benzene; at 0 ℃; for 1.5h; Inert atmosphere;

DOI:10.1055/a-1297-6838

Reference yield: 81.0%

methyl 2-(3,5-bis((2-chlorobenzyl)oxy)-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetyl)phenyl)acetate → methyl-2-(3,5-dihydroxy-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetyl)phenyl)acetate (1263694-22-9)

Guidance literature:

With 20% palladium hydroxide-activated charcoal; hydrogen; In ethyl acetate;

DOI:10.1055/s-0034-1379988

Reference yield:

2,4-bis(benzyloxy)-6-(2,2-dimethoxyethyl)benzaldehyde (1309953-47-6) → methyl-2-(3,5-dihydroxy-2-(2-((2R,6R)-6-methyltetrahydro-2H-pyran-2-yl)acetyl)phenyl)acetate (1263694-22-9)

Guidance literature:

Multi-step reaction with 7 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

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

6: diethyl ether / Inert atmosphere

7: hydrogen; palladium(II) hydroxide / ethyl acetate / 7.5 h / 20 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; Jones reagent; tetrapropylammonium perruthennate; tetrabutyl ammonium fluoride; hydrogen; palladium(II) hydroxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; diethyl ether; dichloromethane; ethyl acetate; acetone; 4: oxy-Michael reaction;

DOI:10.1016/j.tetasy.2012.06.009

upstream raw materials:

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

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

3,5-dibenzyloxybenzyl alcohol