Reaktion #65357

ord-24624ba4ad42404e88c2b51eb4f0dcd5

Reaktionsgleichung

Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1F
6-Amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
→
O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1F
title compound
O=c1[nH]cnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1F
9-(2-Deoxy-2-fluoro-β-D-ribofuranosyl)hypoxanthine

Edukte

Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1F
6-Amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine

Reagenzien

Keine

Lösungsmittel

O
water

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvent was removed under vacuum
  2. 2
    workup.DISSOLUTIONThe residue was dissolved in water/n-propanol (7/3)
  3. 3
    Sonstigechromatographed on a 5×90 cm column of Sephadex
  4. 4
    Sonstigethe solvent removed under vacuum
  5. 5
    workup.DISSOLUTIONThe residue was dissolved in water

Vorschrift

6-Amino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (0.29 g, 1.0 mmole), prepared as in Example 8, was dissolved in 100 ml of water. Calf intestinal adenosine deaminase (4 I.U., Boehringer Mannheim) was added and the solution incubated at 37° C. for 24 hrs. The solvent was removed under vacuum. The residue was dissolved in water/n-propanol (7/3) and chromatographed on a 5×90 cm column of Sephadex G-10 (Pharmacia LKB) with water/n-propanol (7/3) as the solvent. Product-containing fractions were combined and the solvent removed under vacuum. The residue was dissolved in water and lyophilized to obtain title compound that analyzed as a hydrate.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05420115uspto-grants-1995_05