HCID 46223008, compound → Raffinose

HRID 2399223Notes

Reaction equation

HRID 2399223 reaction equation
[CH2:1]([OH:34])[C@H:2]1[O:7][CH:6]([O:8][CH2:9][C@H:10]2[O:15][CH:14]([O:16][C@:17]3([CH2:26][OH:27])[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@@H:18]3[OH:25])[C@H:13]([OH:28])[C@@H:12]([OH:29])[C@@H:11]2[OH:30])[C@H:5]([OH:31])[C@@H:4]([OH:32])[C@H:3]1[OH:33].O.O.O.O.O>CN(C)C=O>[CH2:1]([OH:34])[C@H:2]1[O:7][C@H:6]([O:8][CH2:9][C@H:10]2[O:15][C@H:14]([O:16][C@:17]3([CH2:26][OH:27])[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@@H:18]3[OH:25])[C@H:13]([OH:28])[C@@H:12]([OH:29])[C@@H:11]2[OH:30])[C@H:5]([OH:31])[C@@H:4]([OH:32])[C@H:3]1[OH:33]

Participants

3

Reactant 1

HCID 46223008HCID 46223008, compound

Product 1

HCID 439242RaffinoseYield 311.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2.0 g of D-raffinose pentahydrate in 50 ml of absolute dimethylformamide was stirred at 60° C. for 20 hours in the presence of 10.3 g of sulphur trioxide-trimethylamine complex, whereby a precipitate separated. The solvent was decanted off. The residue was washed with methanol, dissolved in 64 ml of aqueous 10% sodium acetate solution and concentrated. The residue was taken up several times in water and evaporated to remove trimethylamine. The residue was gel-chromatographed (Sephadex® LH 20) in order to remove salts. After freeze-drying there were obtained 5.28 g of sulfated raffinose, S=19.89%, AS (average degree of sulfation) about 2.8.

Workup

  1. customseparated
  2. customThe solvent was decanted off
  3. washThe residue was washed with methanol
  4. dissolutiondissolved in 64 ml of aqueous 10% sodium acetate solution
  5. concentrationconcentrated
  6. customevaporated
  7. customto remove trimethylamine
  8. customThe residue was gel-chromatographed (Sephadex® LH 20) in order
  9. customto remove salts
  10. customAfter freeze-drying there

Sources & evidence

ORD record
ord-6faae3d384ea440d806792d131a363d2
Source dataset
uspto-grants-1995_09
Patent number
US05447919

Reaction notes

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