ChemicalBook CAS DataBase List 4'-Demethylepipodophyllotoxin

4'-Demethylepipodophyllotoxin synthesis

10synthesis methods

Product Name:4'-Demethylepipodophyllotoxin
CAS Number:6559-91-7
Molecular formula:C21H20O8
Molecular Weight:400.38

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6559-91-7
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Yield:6559-91-7 90%

Reaction Conditions:

Stage #1: (-)-podophyllotoxinwith methanesulfonic acid;sodium iodide in dichloromethane at 0 - 20; for 5 h;
Stage #2: with barium carbonate in water monomer;acetone at 40; for 0.5 h;

Steps:

2.4 Example 2: Step Four: Preparationof 4'-O- demethyl podophyllotoxin (V):

The podophyllotoxin 2.1g (5.0mmol) was dissolved in dry methylenechloride, sodium iodide (2.3g, 15.0mmol) Was added to the above solution andstirred for 5 minutes. The reaction solution was cooled to ice-water bath 0 °C, 1.48 Methanesulfonic acid (15.0 mmol) is slowly added dropwise to thereaction mixture and stirring was continued, and then raised to The reactionwas continued at room temperature for 5 hours. Nitrogen, removed HI gasesproduced during the reaction. Then, Reduced pressure in the above reactionsolvent was removed under no processing to the next step. The above crudeproduct Was dissolved in acetone - water (25mL-25mL) mixed solvent was addedbarium carbonate (2.0g, 10.0mmol), For 30 minutes at 40 ° C the reactionconditions, after 100mL of dichloromethane was added to the mixed solution, Thenpour in 500ml of 10% aqueous sodium thiosulfate, and extracted withdichloromethane, the organic phase, dry Dried over sodium sulfate, andconcentrated to give the crude product was purified by silica gelchromatography (eluent: chloroform: methanol = 92: 8), The product was VII1.8g,yield: 90%, white solid.

References:

CN104098594,2016,B Location in patent:Paragraph 0040-0041