Adenine → 9-[2'-Hydroxy-3'-octadecyloxypropyl]-adenine

Beteiligte Stoffe

Reaktionsschritte

A mixture of adenine (0.829 g, 6.10 mmol), anhydrous potassium carbonate (45 mg) and rac-1,2-epoxy-3-octadecyloxypropane (2.0 g, 6.13 mmol) in anhydrous dimethylformamide (10 mL) is stirred at 70°-75° C. for 20 hours under a nitrogen atmosphere. The reaction mixture is filtered directly without cooling, and the filtrate is concentrated in vacuo to afford a white residue. The residue is stirred with 95:5 (v/v) chloroform-methanol. The insoluble solid is filtered, purified by chromatography, and dried in vacuo to give 0.9 g (31.8%) of 9-[2'-hydroxy-3'-octadecyloxypropyl]-adenine (CPR 1148): Thin-layer Chromatography (TLC); 4×8 cm silica gel 60, 0.25 mm thickness, 10:2:0.2 (v/v/v) CHCl3 -CH3OH-30% aqueous ammonia (Rf value=0.65); mp 151°-152° C.

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