4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester

Base Information

• Chemical Name: 4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester
• CAS No.: 915789-27-4
• Molecular Formula: C₂₉H₂₄O₈
• Molecular Weight: 500.505
• Mol file: 915789-27-4.mol

Synonyms:4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester

Chemical Property of 4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester

There total 13 articles about 4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester 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: 76.0%

4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester (915789-25-2) + acrolein (107-02-8,25068-14-8) → 4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester (915789-27-4)

Guidance literature:

Hoveyda-Grubbs catalyst second generation; In dichloromethane; Heating;

DOI:10.1021/ol062233m

Reference yield:

ethyl orselinate (2524-37-0) → 4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester (915789-27-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 88 percent / K₂CO₃*1.5H₂O / acetone / 24 h / Heating

2: 95 percent / K₂CO₃ / acetone / Heating

3: 100 percent / KOH / ethanol; H₂O / Heating

4: oxalyl chloride; DMF / CH₂Cl₂ / 0 - 20 °C

5: 136 mg / 4-dimethylaminopyridine; iPr₂NEt / CH₂Cl₂ / 20 °C

6: 76 percent / Hoveyda-Grubbs 2-nd generation catalyst / CH₂Cl₂ / Heating

With dmap; potassium hydroxide; oxalyl dichloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; Hoveyda-Grubbs catalyst second generation; In ethanol; dichloromethane; water; acetone;

DOI:10.1021/ol062233m

Reference yield:

6-ethynyl-2,4-dihydroxy-3-methylbenzaldehyde (915789-22-9) → 4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-3-oxo-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester (915789-27-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 86 percent / CuI; Et₃N / Pd(PPh₃)4 / tetrahydrofuran / 20 °C

2: [(-)-sparteine]2Cu₂O₂ complex; diisopropylethylamine; 4-dimethylaminopyridine / CH₂Cl₂ / 30 h / -10 °C

3: 77 percent / CuI; diisopropylethylamine / CH₂Cl₂ / 1 h / 20 °C

4: 136 mg / 4-dimethylaminopyridine; iPr₂NEt / CH₂Cl₂ / 20 °C

5: 76 percent / Hoveyda-Grubbs 2-nd generation catalyst / CH₂Cl₂ / Heating

With dmap; copper(l) iodide; [(-)-sparteine]2Cu₂O₂; triethylamine; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Hoveyda-Grubbs catalyst second generation; In tetrahydrofuran; dichloromethane; 1: Sonogashira coupling;

DOI:10.1021/ol062233m

upstream raw materials:

4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-7-methyl-6,8-dioxo-3-((E)-propenyl)-7,8-dihydro-6H-isochromen-7-yl ester

acrolein

6-ethynyl-2,4-dihydroxy-3-methylbenzaldehyde

(R,E)-7-hydroxy-7-methyl-3-(prop-1-en-1-yl)-6H-isochromene-6,8(7H)-dione

Downstream raw materials:

(-)-mitorubrinol

4-Benzyloxy-2-methoxy-6-methyl-benzoic acid (R)-3-((E)-3-hydroxy-propenyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl ester

Refernces