Reaktion #539760

Reaktionsgleichung

9-(3-O-Benzyl-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-2-O-trifluoromethanesulfonyl-β-D-erythro-pentofuranosyl)-6-N-benzoyladenine

lithiumiodide

→

foam

Ausbeute 90.0%

9-(3-O-Benzyl-2-deoxy-2-iodo-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-β-D-threo-pentofuranosyl)-6-N-benzoyladenine

Ausbeute 90.0%

Lösungsmittel

acetonitrile

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturheated to reflux
2. 2
   SonstigeSolvent was removed in vacuo
3. 3
   Sonstigethe residue was partitioned between DCM (50 ml) and water (50 ml)
4. 4
   SonstigeLayers were separated
5. 5
   Waschenthe organic layer was washed with brine (50 ml)
6. 6
   Trocknendried (Na2SO4)
7. 7
   Filtrationfiltered
8. 8
   Sonstigethe solvent removed in vacuo

Vorschrift

9-(3-O-Benzyl-5-O-methanesulfonyl-4-C-(methanesulfonyloxymethyl)-2-O-trifluoromethanesulfonyl-β-D-erythro-pentofuranosyl)-6-N-benzoyladenine (589 mg, 0.755 mmol) was dissolved in dry acetonitrile (15 ml), added lithiumiodide (202 mg, 2 equiv.) and heated to reflux. After 2 hrs, LCMS shows full conversion. Solvent was removed in vacuo and the residue was partitioned between DCM (50 ml) and water (50 ml). Layers were separated and the organic layer was washed with brine (50 ml), dried (Na2SO4), filtered and the solvent removed in vacuo to afford an orange foam (514 mg, 90% yield)

Quelle