Epipinoresinol → Pinoresinol diglucoside

Temperatur

25 °C

Pinoresinol-diglucoside - Silver oxide (2.24 g, 9.65 mmol) was added to a stirred reaction mixture of pinoresinol (358 mg, 1 mmol) and aceto-α bromo glucose (2.24 g, 5.45 mmol) in 6 ml of dry quinoline over a period of 15 min. After stirring the reaction mixture for 16 hours at 25° C., the reaction mixture was extracted with 20 ml of ether. The organic ethereal layer was successively washed with water (2 × 10 ml), 1 N HCl (5 × 5 ml), dilute NaHCO3 (3 × 5 ml) and dried over Na2SO4. After evaporation of the organic solvent in vacuo, the residue was dissolved in 20 ml of methanol containing 1 ml of 5 N NaOH and the mixture was stirred for 2 hours at 0° C. After acidification to pH 4.5 with 2N HCl, this mixture was evaporated to dryness. The residue was dissolved in 5 ml of water and chromatographed over an Amberlite XAD-2 column (1.9 × 38 cm). The column was washed with 150 ml of water to remove salts. The diglucoside was then eluted off the column with 250 ml of 20% aqueous acetone. The combined acetone fractions were evaporated to dryness and the residue was chromatographed over a silica-gel column (3.5 × 44 cm). Elution of the column with solvent system, CHCl3 :CH3OH:H2O (65:30:10) gave 230 mg (34%) of pure pinoresinol diglucoside, m.p. 238-250°; uv (H2O) 276 nm (ε6,600) and 226 (ε21,900); [α]D25 -15.3° (c, 0.4, H2O); IR (KBr) 1600, 1515, 1414, 1275, 1260, 1230, 1080, 1050, 1030, 993 810 cm-1. Anal calcd for C32H42O16.4H2O: C, 50.92; H, 6.68. Found: C, 50.70; H, 6.70.

1. extractionthe reaction mixture was extracted with 20 ml of ether
2. washThe organic ethereal layer was successively washed with water (2 × 10 ml), 1 N HCl (5 × 5 ml), dilute NaHCO3 (3 × 5 ml)
3. dry with materialdried over Na2SO4
4. customAfter evaporation of the organic solvent in vacuo
5. dissolutionthe residue was dissolved in 20 ml of methanol containing 1 ml of 5 N NaOH
6. stirringthe mixture was stirred for 2 hours at 0° C
7. customAfter acidification to pH 4.5 with 2N HCl, this mixture was evaporated to dryness
8. dissolutionThe residue was dissolved in 5 ml of water
9. customchromatographed over an Amberlite XAD-2 column (1.9 × 38 cm)
10. washThe column was washed with 150 ml of water
11. customto remove salts
12. washThe diglucoside was then eluted off the column with 250 ml of 20% aqueous acetone
13. customThe combined acetone fractions were evaporated to dryness
14. customthe residue was chromatographed over a silica-gel column (3.5 × 44 cm)
15. washElution of the column with solvent system, CHCl3 :CH3OH:H2O (65:30:10)

ORD-Eintrag

ord-43b1f373270646548fbc391ac43d91a7

Quelldatensatz

uspto-grants-1978_07

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US04103006