Studies on Aminosugars. XXIX. Syntheses of Nucleosides of 3-Amino-3-deoxy-3-C-hydroxymethyl-β-d-ribofuranose

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Abstract
Reduction of 3-acetamido-3-C-carboxy-3-deoxy-1,2-O-isopropylidene-α-d-ribofuranose-y-lactone (1) with lithium aluminum hydride or sodium borohydride followed by acetylation gave 3-acetamido-3-C-acetoxymethyl-5-O-acetyl-3-deoxy-1,2-O-isopropylidene-α-d-ribofuranose (2). Hyrdolysis of 2 followed by N-phthaloylation and O-acetylation gave 3-C-acetoxymethyl-5-O-acetyl-3-deoxy-1,2-O-isopropylidene-3-phthalimido-α-d-ribo-furanose (7), which was acetolyzed and chlorinated to give acylglycosyl chloride (9). Condensation of 9 with 6-benzamidopurine followed by aminolysis afforded 9-(3′-amino-3′-deoxy-3′-C-hydroxymethyl-β-d-ribofuranosyl) adenine (11). 6-dimethylaminopurine, guanine, cytosine and uracil derivatives were similarly synthesized.