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Trimethyl Phosphate → Ascorbic acid 2-phosphate

HRID 1195247
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1195247
CC1(C)[O:6][C@H:5]([C@H:7]2[O:12][C:10](=[O:11])[C:9]([OH:13])=[C:8]2[OH:14])[CH2:4][O:3]1.O=C1O[C@H]([C@H](CO)O)C(O)=C1O.C[O:29][P:30](=O)([O:33]C)[O:31]C.[OH-].[Ca+2].[OH-].P(Cl)(Cl)(Cl)=O>O.N1C=CC=CC=1.CC(C)=O.CN(C)C=O>[P:30]([O:13][C:9]1[C:10]([O:12][C@H:7]([C@H:5]([CH2:4][OH:3])[OH:6])[C:8]=1[OH:14])=[O:11])([OH:33])([OH:31])=[O:29]
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Komponenten

10

Edukt 5

HCID 10541Trimethyl PhosphateHCID 24813Phosphorus oxychlorideHCID 6093208Calcium HydroxideHCID 54670067L-Ascorbic Acid2×HCID 54691418L-Ascorbic acid, 5,6-O-(1-methylethylidene)-2×

Produkt 1

HCID 54679073Ascorbic acid 2-phosphate

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittel2×HCID 962WaterLösungsmittel4×HCID 1049PyridineLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

The above-described method is to react 5,6-isopropylidene-L-ascorbic acid or L-ascorbic acid with a phosphoric halide in a specific solvent (such as water, or a mixed solvent composed of water and acetone, dimethylformamide or trimethylphosphoric acid) in the presence of a base at temperature not higher than room temperature. More particularly, L-ascorbic derivative of which the hydroxyl groups at the 5- and 6-positions have been protected with acetone under acidic conditions (i.e., 5,6-isopropylidene-L-ascorbic acid) or L-ascorbic acid is dissolved in a mixed solvent composed of water and pyridine or a mixture of water and calcium hydroxide, and phosphorus oxychloride is added dropwise to the resulting solution or mixture at a temperature not higher than 0° C., and the reaction is continued at the same temperature for 90 minutes (reaction ratios: 94.5% and 70.6%, respectively). Then, the reaction mixture is treated with Amberlite Resin IR-120 (H+ -form) at room temperature to desalt the product, followed by neutralization with magnesium oxide, removal of the solvent by distillation, dropwise addition of ethanol to the residue to obtain white powder of magnesium salt of L-ascorbic acid 2-phosphate, which is recrylstallized from water-ethanol (yields: 75.1% and 55.3%, respectively).

Aufarbeitung

  1. customhigher than room temperature
  2. dissolutionis dissolved in a mixed solvent
  3. additionis added dropwise to the resulting solution or mixture at a temperature not higher than 0° C.
  4. custom(reaction ratios
  5. additionThen, the reaction mixture is treated with Amberlite Resin IR-120 (H+ -form) at room temperature
  6. customfollowed by neutralization with magnesium oxide, removal of the solvent by distillation, dropwise addition of ethanol to the residue

Quellen und Nachweise

ORD-Eintrag
ord-959567bc198444f4b9035fa5607157b3
Quelldatensatz
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05110951

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