Methanol, 1,1-diethoxy-, 1-acetate → 1,4-Anhydro-2-(6-chloro-9H-purin-9-yl)-2,3-dideoxypentitol

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Reaction Steps

A solution of (2R-cis)-4-[(5-amino-6-chloro-4-pyrimidinyl)amino]tetrahydro-2-furanmethanol, Compound IX, (220 mg, 0.90 mmole) and diethoxymethylacetate (5 mL) in a 10 mL round bottom flask fitted with a reflux condenser was heated to 100° for 120 hours. The volatile materials were removed via rotary evaporation, and the residue was recombined with toluene (5 mL) and p-toluenesulphonic acid (5 mg). After stirring at room temperature for one hour and by flash column chromatography (10% MeOH/90% CH2Cl2) to afford 109 mg (48%) of Compound X as a white solid:

Provenance & Evidence