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

Base Information

Chemical Name: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
CAS No.:915789-26-3
Molecular Formula:C₂₉H₂₆O₈
Molecular Weight:502.521
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 14 articles about 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 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: 66.0%

: 915789-27-4
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

: 915789-26-3
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

Guidance literature:: With boron trifluoride diethyl etherate; diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃; for 0.5h;
DOI:10.1021/ol062233m

Reference yield:

: 2524-37-0
ethyl orselinate

: 915789-26-3
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

Guidance literature:: Multi-step reaction with 7 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

7: 66 percent / BF₃*OEt₂; DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

With dmap; potassium hydroxide; oxalyl dichloride; boron trifluoride diethyl etherate; diisobutylaluminium hydride; potassium carbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; Hoveyda-Grubbs catalyst second generation; In ethanol; hexane; dichloromethane; water; acetone;
DOI:10.1021/ol062233m

Reference yield:

: 915789-22-9
6-ethynyl-2,4-dihydroxy-3-methylbenzaldehyde

: 915789-26-3
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

Guidance literature:: Multi-step reaction with 6 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

6: 66 percent / BF₃*OEt₂; DIBAL-H / CH₂Cl₂; hexane / 0.5 h / -78 °C

With dmap; copper(l) iodide; [(-)-sparteine]2Cu₂O₂; boron trifluoride diethyl etherate; diisobutylaluminium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Hoveyda-Grubbs catalyst second generation; In tetrahydrofuran; hexane; dichloromethane; 1: Sonogashira coupling;
DOI:10.1021/ol062233m