Thymidine → 9-(2,3-dideoxy-3-fluoro-beta-D-erythro-pentofuranosyl)-6-(hexylamino)-9H-purine

HRID 1376446ノート

反応式

HRID 1376446 の反応式
[CH2:1]([NH:7][C:8]1[N:16]=[CH:15][N:14]=[C:13]2[C:9]=1[N:10]=[CH:11][NH:12]2)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[F:17][C@@H:18]1[C@@H:22]([CH2:23][OH:24])[O:21][C@@H:20](N2C=CC(=O)NC2=O)[CH2:19]1.[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+].CO>[F:17][C@@H:18]1[C@@H:22]([CH2:23][OH:24])[O:21][C@@H:20]([N:12]2[CH:11]=[N:10][C:9]3[C:13]2=[N:14][CH:15]=[N:16][C:8]=3[NH:7][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])[CH2:19]1

参加物

7

反応物 4

HCID 5789ThymidineHCID 1624502',3'-Dideoxy-3'-fluorouridineHCID 10290740Potassium azideHCID 178444747HCID 178444747、化合物

生成物 1

HCID 677039649-(2,3-dideoxy-3-fluoro-beta-D-erythro-pentofuranosyl)-6-(hexylamino)-9H-purine収率 29.6%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 62657Potassium Phosphate, Tribasic溶媒

反応条件

温度
45 °C

実験手順

6-Hexylamino-9H-purine (0.67 g, 2.6 mmoles, Sigma Chemical Company) and 2',3'-dideoxy-3'-fluorouridine (0.50 g, 2.2 mmoles) were suspended in potassium phosphate buffer (50 ml, 10 mM), pH 7.0, containing 0.04% potassium azide. Purine nucleoside phosphorylase (1120 I.U.) and thymidine phosphorylase (10,000 I.U.) (Krenitsky, et al., Biochemistry, 20, 3615 (1981) and U.S. Pat. No. 4,381,344) immobilized on DEAE cellulose was added to the reaction and the suspension was stirred at 45° C. After 4 days, MeOH (175 ml) was added to the reaction. The reaction was applied to a column containing product were pooled, concentrated, and flash chromatographed on silica gel (2.5×20 cm) with dichloromethane:acetone (92:8). Fractions containing product were pooled, concentrated, and then flash chromatographed again on silica gel (2.5×20 cm) with dichloromethane:acetone (9:1). Solvent was removed and lyophilization yielded 9-(2,3-dideoxy-3-fluoro-β-D-erythro-pentofuranosyl)-6-(hexylamino)-9H-purine (29%) (0.22 g): mp 83° C.;

後処理

  1. additionwas added to the reaction
  2. additioncontaining product
  3. concentrationconcentrated
  4. customflash chromatographed on silica gel (2.5×20 cm) with dichloromethane:acetone (92:8)
  5. additionFractions containing product
  6. concentrationconcentrated
  7. customflash chromatographed again on silica gel (2.5×20 cm) with dichloromethane:acetone (9:1)
  8. customSolvent was removed

出典と根拠

ORDレコード
ord-2c82d9ad36f847518d4b287323530f1c
出典データセット
uspto-grants-1997_09
特許番号
US05663154

反応ノート

読み込み中…