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llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
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Trimethyl Phosphate → Ascorbic acid 2-phosphate

HRID 1195247
ノート
印刷プレビュー

反応式

HRID 1195247 の反応式
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]
参加物実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

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

生成物 1

HCID 54679073Ascorbic acid 2-phosphate

試薬・触媒・溶媒

4
HCID 180Acetone溶媒2 回HCID 962Water溶媒4 回HCID 1049Pyridine溶媒HCID 6228Dimethylformamide溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-959567bc198444f4b9035fa5607157b3
出典データセット
uspto-grants-1992_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05110951

反応ノート

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