3''-HYDROXYMITORUBRIN

Base Information

• Chemical Name: 3''-HYDROXYMITORUBRIN
• CAS No.: 3215-47-2
• Molecular Formula: C21H18 O8
• Molecular Weight: 398.369
• Mol file: 3215-47-2.mol

Synonyms:Benzoicacid, 2,4-dihydroxy-6-methyl-,(7R)-7,8-dihydro-3-[(1E)-3-hydroxy-1-propenyl]-7-methyl-6,8-dioxo-6H-2-benzopyran-7-ylester (9CI); Benzoic acid, 2,4-dihydroxy-6-methyl-,7,8-dihydro-3-(3-hydroxy-1-propenyl)-7-methyl-6,8-dioxo-6H-2-benzopyran-7-ylester, [R-(E)]-; b-Resorcylicacid, 6-methyl-, 7-ester with7-hydroxy-3-(3-hydroxypropenyl)-7-methyl-6H-2-benzopyran-6,8(7H)-dione(7CI,8CI); 6H-2-Benzopyran-6,8(7H)-dione,7-hydroxy-3-(3-hydroxypropenyl)-7-methyl-, 7-(6-methyl-b-resorcylate) (8CI);(-)-Mitorubrinol; Mitorubrinol

Chemical Property of 3''-HYDROXYMITORUBRIN

Chemical Property:

• PSA: 130.36000
• LogP: 1.74640

Purity/Quality:

99%min ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3''-HYDROXYMITORUBRIN

There total 14 articles about 3''-HYDROXYMITORUBRIN 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: 72.0%

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 (915789-26-3) → (-)-mitorubrinol (3215-47-2)

Guidance literature:

With boron trichloride; In dichloromethane; at -20 ℃; for 2h;

DOI:10.1021/ol062233m

Reference yield:

ethyl orselinate (2524-37-0) → (-)-mitorubrinol (3215-47-2)

Guidance literature:

Multi-step reaction with 8 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

8: 72 percent / BCl₃ / CH₂Cl₂ / 2 h / -20 °C

With dmap; potassium hydroxide; oxalyl dichloride; boron trifluoride diethyl etherate; boron trichloride; 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:

6-ethynyl-2,4-dihydroxy-3-methylbenzaldehyde (915789-22-9) → (-)-mitorubrinol (3215-47-2)

Guidance literature:

Multi-step reaction with 7 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

7: 72 percent / BCl₃ / CH₂Cl₂ / 2 h / -20 °C

With dmap; copper(l) iodide; [(-)-sparteine]2Cu₂O₂; boron trifluoride diethyl etherate; boron trichloride; 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

upstream raw materials:

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

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

2,4-Dihydroxy-3-methyl-6-((E)-pent-3-en-1-ynyl)-benzaldehyde

Refernces