142217-81-0

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• Synthesis

  In a 1-liter round-bottom flask equipped with an argon inlet, [1S-(1α,2β,3α,5β)]-5-[2-amino-6-(phenylmethoxy)-2-(phenylformyl)methyl]cyclopentanemethanol (18, X=BnO) (2.6 g, 4.4 mmol), trimethyl orthoformate (2.38 mL, 21.8 mmol), pyridinium p-toluenesulfonate (0.56 g, 2.22 mmol), and DCM (20 mL) were added with a magnetic stirrer. The reaction mixture was stirred at room temperature for about 16 hours. After the reaction was complete, the reaction mixture was quenched with sodium bicarbonate solution (50 mL). The resulting mixture was extracted with ethyl acetate (2 x 50 mL), the combined organic layers were washed with brine (50 mL), dried (sodium sulfate), and concentrated under vacuum to give the orthoformate intermediate. The crude product was dissolved in acetic acid/acetic anhydride (1.5 mL/30 mL) in a round-bottom flask. The solution was heated to reflux for approximately 5 hours and then cooled to room temperature. Acetic acid/acetic anhydride was removed by vacuum distillation to give an intermediate mixture (2.34 g). The above intermediate mixture (2.2 g, 3.7 mmol) was dissolved in acetonitrile (60 mL) and 2N HCl (30 mL) and then heated to reflux to complete the reaction. The mixture was cooled to room temperature and neutralized by adding triethylamine. The mixture was directly concentrated under vacuum to remove most of the acetonitrile. Ethanol was added to the resulting solid residue, and the suspension was stirred for 1 hour. The solid was collected by filtration, washed with ethanol, and dried under high vacuum to give 1.57 g of the title compound 2-amino-2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one, in 93% yield. The synthetic route is shown in Figure 2.

  

  Figure 2. Synthetic route of 2-Amino-1,9-dihydro-9-[(1S,3R,4S)-4-(benzyloxy)-3-(benzyloxymethyl)-2-methylenecyclopentyl]-6H-purin-6-one.;

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