Potassium Carbonate → 2-o-beta-d-Glucopyranosyl-l-ascorbic acid

HRID 548536Notes

Reaction equation

HRID 548536 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:26]([O:28][C@H:29]([C@H:32]([CH2:34][OH:35])[OH:33])[C:30]=1[OH:31])=[O:27])(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O>[C@@H:6]1([O:24][C:25]2[C:26]([O:28][C@H:29]([C@H:32]([CH2:34][OH:35])[OH:33])[C:30]=2[OH:31])=[O:27])[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 546818862-o-(2,3,4,6-Tetra-o-acetyl-beta-d-glucopyranosyl)ascorbic acid

Product 1

HCID 547068332-o-beta-d-Glucopyranosyl-l-ascorbic acidYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

After dissolving 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)ascorbic acid (300 mg, 0.6 mmol) in methanol (10 ml), a solution of potassium carbonate (600 mg) in water (9 ml) was added and the mixture was stirred for 30 minutes. The reaction solution was neutralized with IR-120(H+), the resin was filtered off, and washing was performed with methanol and a 50% methanol aqueous solution. The filtrate and washing solution were combined and concentrated, and then water was added and the mixture was lyophilized to obtain 2-O-(β-D-glucopyranosyl)ascorbic acid as amorphous crystals (190 mg; 100% yield).

Workup

  1. filtrationthe resin was filtered off
  2. washwashing
  3. washThe filtrate and washing solution
  4. concentrationconcentrated
  5. additionwater was added

Sources & evidence

ORD record
ord-78b48b1b1d694809b9d8a9572cd70be4
Source dataset
uspto-grants-2011_05
Patent number
US07943583B2

Reaction notes

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