Reaktion #65346

ord-7aa613c29b004721978c946d018d6d83

Reaktionsgleichung

Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3F)c2n1
2,6-Diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine
Nc1ncnc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
adenosine
→
Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2F)c(=O)[nH]1
title compound
Nc1nc2c(ncn2[C@@H]2O[C@H](CO)[C@@H](O)[C@H]2F)c(=O)[nH]1
9-(2-Deoxy-2-fluoro-β-D-ribofuranosyl)guanine

Edukte

Nc1nc(N)c2ncn([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3F)c2n1
2,6-Diamino-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

Temperatur
4°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.WAITAfter 3 hrs
  2. 2
    Filtrationthe suspension was filtered
  3. 3
    Sonstigeto remove the first batch of product crystals
  4. 4
    Temperaturthe suspension cooled to 4° C
  5. 5
    FiltrationThe suspension was filtered
  6. 6
    Sonstigeto remove the second batch of product crystals

Vorschrift

2,6-Diamino-9-(2-deoxy-2-fluoro-β-D-ribofuranosyl)-9H-purine (0.20 g, 0.64 mmole), prepared as in Example 6, was dissolved in 15 ml of water. Calf intestinal adenosine deaminase (4 I.U., Boehringer Mannheim) was added and the solution incubated at 37° for 4 days. The solution was cooled to 4° C. After 3 hrs, the suspension was filtered to remove the first batch of product crystals. The volume of the filtrate was reduced under vacuum and the suspension cooled to 4° C. The suspension was filtered to remove the second batch of product crystals. The batches of product crystals were combined, suspended in water and lyophilized to obtain title compound that analyzed as a 1.3 hydrate.

Quelle

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