Oxygen → HCID 22841876, compound

HRID 1461459Notes

Reaction equation

HRID 1461459 reaction equation
[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C@@H:17]1[O:38][C@H:37]([CH2:39][OH:40])[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])=[O:4].O=O.[C:43](=O)(O)[O-:44].[Na+]>O.[Pt]>[CH3:1][O:2][C:3]([CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][O:16][C@@H:17]1[O:38][C@H:37]([C:39]([O:44][CH3:43])=[O:40])[C@@H:32]([O:33][C:34](=[O:36])[CH3:35])[C@H:23]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C@H:18]1[O:19][C:20](=[O:22])[CH3:21])=[O:4]

Participants

6

Reactant 3

HCID 977OxygenHCID 516892Sodium BicarbonateHCID 54218895HCID 54218895, compound

Product 1

HCID 22841876HCID 22841876, compound

Reagents, catalysts & solvents 2

HCID 23939PlatinumCatalystHCID 962WaterSolvent

Procedure

A solution of 10 (500 mg)-in 20 mL of water was vigorously stirred with freshly prepared platinum black (200 mg) at 85 C. while oxygen was slowly passed through the suspension. The pH of the reaction was maintained at approximately 8.0 with solid sodium bicarbonate. It took about 2 hours to complete the oxidation. The mixture was cooled after an additional 10 minutes of stirring. After removal of the catalyst by passing the solution through a Nylon-66 0.45 μm pore size filter, the filtrate was lyophilized. The residue was redissolved in 20 mL of ice-water and the solution was adjusted to pH 2 with 12N HCl and extracted with chloroform. The extract was washed with water until neutral, dried over sodium sulfate and concentrated, and the residue was esterfied with ethereal diazomethane. The product was eluted from a column of silica gel (Rf 0.45, hexane-ethyl acetate, 75:25) to give amorphous methyl 1-O-(11-methoxycarbonylundecyl)-3-O-benzyl-2,4-di-O-acetyl-β-D-glucopyranosuronate (11).1H-NMR data: 7.26-7.30 (m, 5 H, arom.), 5.20 (t, 1 H), 5.08 (t,1 H), 4.62(s, 2 H, CH2Bn), 4.45(d, 1 H, anom.), 3.85-3.97 (m, 2 H) 3.73 (s,3 H, COOMe), 3.68(s, 3 H, COOMe), 2.36(t, 2 H, CH2 lipid), 1.98(s, 6 H, 2Ac), 1.20-1.63 (18 H, lipid).

Workup

  1. temperatureThe mixture was cooled after an additional 10 minutes
  2. customAfter removal of the catalyst
  3. filtrationfilter
  4. dissolutionThe residue was redissolved in 20 mL of ice-water
  5. extractionextracted with chloroform
  6. washThe extract was washed with water until neutral,
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. washThe product was eluted from a column of silica gel (Rf 0.45, hexane-ethyl acetate, 75:25)

Sources & evidence

ORD record
ord-58f54172094f46f6bf5a7d78457b259d
Source dataset
uspto-grants-1991_12
Patent number
US05075433

Reaction notes

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