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

HRID 37072

반응식

HRID 37072 반응식
[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]

참가 물질

6

반응물 4

HCID 5789Thymidine2회HCID 706326-Methoxy-9H-purineHCID 1508512'Fluoro-2'-deoxyuridineHCID 10290740Potassium azide2회

생성물 1

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

시약·촉매·용매 1

HCID 62657Potassium Phosphate, Tribasic용매2회

반응 조건

온도
37 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c6ac922990654a2baa45ba3d39e0912e
출처 데이터셋
uspto-grants-1995_05
특허 번호
US05420115

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