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Abstract

1-(Adenin-9-yl)-1-deoxy-DL-ribitol (III), -D-arabitol (IXa), -L-arabitol (XIVa), -DL-xylitol (XXIVa), 1-(cytosin-L-yl)-1-deoxy-D-arabitol (IXb), -L-arabitol (XIVb), 1-(uracil-1-yl)-1-deoxy-D-arabitol (IXc), -L-arabitol (XIVc) and -DL-xylitol (XXIVb) were prepared by reaction of 1-O-p-toluenesulfonyl-2,3:4,5-di-O-isopropylidenealditols Ib, VIIb, XIIb and XXIIb with sodium salts of adenine, N⁴-benzoylcytosine or 4-methoxy-2-pyrimidone followed by removal of the protecting groups. Condensation of the mentioned sodium salts with methyl 5-O-p-toluenesulfonyl-2,3-O-isopropylidene-β-D-ribofuranoside (IV) with subsequent acid hydrolysis and reduction with sodium borohydride afforded 1-(adenin-9-yl)-1-deoxy-L-ribitol (VIa) and 1-(cytosin-1-yl)-1-deoxy-L-ribitol (VIb). 1-(Adenin-9-yl)-1-deoxy-L-lyxitol (XVII), -L-lyxitol (XVIII) and -2-O-methyl-D-lyxitol (XXI) were prepared analogously. Acid hydrolysis of 5-(adenin-9-yl)-5-deoxy-4-O-benzyl-1,2-O-isopropylidene-α-D-xylofuranose (XXVa), followed by reduction with sodium borohydride and catalytic hydrogenation, gave 1-(adenin-9-yl)-1-deoxy-L-xylitol (XXVIb).