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Thymidine → 9-(2-Deoxy-2-fluoro-beta-D-ribofuranosyl)-6-methoxy-9H-purine

HRID 37072
ノート
印刷プレビュー

反応式

HRID 37072 の反応式
[CH3:1][O:2][C:3]1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2.[F:12][C@@H:13]1[C@H:17]([OH:18])[C@@H:16]([CH2:19][OH:20])[O:15][C@H:14]1N1C=CC(=O)NC1=O.[N-]=[N+]=[N-].[K+].[C@@H]1(N2C=C(C)C(=O)NC2=O)O[C@H](CO)[C@@H](O)C1>P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[F:12][C@@H:13]1[C@H:17]([OH:18])[C@@H:16]([CH2:19][OH:20])[O:15][C@H:14]1[N:7]1[CH:6]=[N:5][C:4]2[C:8]1=[N:9][CH:10]=[N:11][C:3]=2[O:2][CH3:1]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 5789Thymidine2 回HCID 706326-Methoxy-9H-purineHCID 1508512'Fluoro-2'-deoxyuridineHCID 10290740Potassium azide2 回

生成物 1

HCID 99711009-(2-Deoxy-2-fluoro-beta-D-ribofuranosyl)-6-methoxy-9H-purine

試薬・触媒・溶媒 1

HCID 62657
Potassium Phosphate, Tribasic
溶媒
2 回

反応条件

温度
37 °C

実験手順

6-Methoxypurine (Sigma Chemical Company; 0.8 g, 5.3 mmoles) and 1-(2-deoxy-2-fluoro-β-D-ribofuranosyl)uracil (0.4 g, 1.6 mmoles) which may be prepared according to J. F. Codington et al. (J. Org. Chem. 29:558, 1964) were suspended in 20 ml of 10 mM potassium phosphate buffer, pH 7.0, which contained 0.04% (w/v) potassium azide. Thymidine phosphorylase (2,400 I.U.) and purine nucleoside phosphorylase (3,900 I.U.) (T. A. Krenitsky et al., Biochemistry 20:3615, 1981 and U.S. Pat. No. 4,381,344) were added and the suspension stirred at 37° C. On day 6 the reaction was diluted to 100 ml with 5 mM potassium phosphate buffer, pH 7.0, which contained 0.04% (w/v) potassium azide. On day 16, 2,640 I.U. thymidine phosphorylase and 4,360 I.U. purine nucleoside phosphorylase were added. On day 45, the reaction was evaporated. The residue was suspended in warm methanol and the suspension was filtered. The filtrate was evaporated. The residue was dissolved in warm water and applied to a 2.5×7 cm column of anion exchange resin (Bio-Rad AG1X2-hydroxide form). After washing with water, the product was eluted with methanol/water (9/1). Product-containing fractions were combined and the solvent removed under vacuum. The residue was dissolved in water and lyophilized to obtain title compound which analyzed as a 0.3 hydrate.

後処理

  1. addition4,381,344) were added
  2. waitOn day 16, 2,640 I.U
  3. waitOn day 45
  4. customthe reaction was evaporated
  5. filtrationthe suspension was filtered
  6. customThe filtrate was evaporated
  7. dissolutionThe residue was dissolved in warm water
  8. washAfter washing with water
  9. washthe product was eluted with methanol/water (9/1)
  10. customthe solvent removed under vacuum
  11. dissolutionThe residue was dissolved in water

出典と根拠

ORDレコード
ord-c6ac922990654a2baa45ba3d39e0912e
出典データセット
uspto-grants-1995_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05420115

反応ノート

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