4-benzyloxy-2-methoxy-6-methyl-benzoic acid 3-(2-tert-butoxycarbonyl-vinyl)-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 3-(2-tert-butoxycarbonyl-vinyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl ester
CAS No.:915789-28-5
Molecular Formula:C₃₃H₃₂O₉
Molecular Weight:572.612
Hs Code.:

4-benzyloxy-2-methoxy-6-methyl-benzoic acid 3-(2-<i>tert</i>-butoxycarbonyl-vinyl)-7-methyl-6,8-dioxo-7,8-dihydro-6<i>H</i>-isochromen-7-yl ester

Synonyms:4-benzyloxy-2-methoxy-6-methyl-benzoic acid 3-(2-tert-butoxycarbonyl-vinyl)-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 3-(2-tert-butoxycarbonyl-vinyl)-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 3-(2-tert-butoxycarbonyl-vinyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl ester

There total 13 articles about 4-benzyloxy-2-methoxy-6-methyl-benzoic acid 3-(2-tert-butoxycarbonyl-vinyl)-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: 90.0%

: 915789-25-2
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

: 1663-39-4,25232-27-3
tert-Butyl acrylate

: 915789-28-5
4-benzyloxy-2-methoxy-6-methyl-benzoic acid 3-(2-tert-butoxycarbonyl-vinyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl ester

Guidance literature:: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; Heating;
DOI:10.1021/ol062233m

Reference yield:

: 2524-37-0
ethyl orselinate

: 915789-28-5
4-benzyloxy-2-methoxy-6-methyl-benzoic acid 3-(2-tert-butoxycarbonyl-vinyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl ester

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: 90 percent / Grubbs 2-nd generation catalyst / CH₂Cl₂ / Heating

With dmap; potassium hydroxide; oxalyl dichloride; potassium carbonate; N-ethyl-N,N-diisopropylamine; N,N-dimethyl-formamide; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In ethanol; dichloromethane; water; acetone;
DOI:10.1021/ol062233m

Reference yield:

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

: 915789-28-5
4-benzyloxy-2-methoxy-6-methyl-benzoic acid 3-(2-tert-butoxycarbonyl-vinyl)-7-methyl-6,8-dioxo-7,8-dihydro-6H-isochromen-7-yl ester

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: 90 percent / Grubbs 2-nd generation catalyst / CH₂Cl₂ / Heating

With dmap; copper(l) iodide; [(-)-sparteine]2Cu₂O₂; triethylamine; N-ethyl-N,N-diisopropylamine; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; dichloromethane; 1: Sonogashira coupling;
DOI:10.1021/ol062233m