Collect. Czech. Chem. Commun. 1989, 54, 2753-2766

Utilization of 1,6-anhydrohexoses for the preparation of some aliphatic adenosine analogs

Marcela Krečmerováa, Miloslav Černýb, Miloš Buděšínskýa and Antonín Holýa

a Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6
b Department of Organic Chemistry, Charles University, 128 40 Prague 2


Reaction of sodium salt of adenine with 1,6:3,4-dianhydro-2-O-p-toluenesulfonyl-β-D-galactopyranose (I) afforded 4-(adenin-9-yl)-1,6:2,3-dianhydro-4-deoxy-β-D-mannopyranose (II) and 2,4-bis(adenin-9-yl)-1,6-anhydro-2,4-dideoxy-β-D-glucopyranose (IV). Compound II was converted into 4-(adenin-9-yl)-1,6-anhydro-4-deoxy-β-D-glucopyranose (VI). Cleavage of the 1,6-anhydro bond in this compound with hot concentrated hydrochloric acid led to 4-(adenin-9-yl)-4-deoxy-D-glucose (VIII) which was reduced with sodium borohydride to give 4-(adenin-9-yl)-4-deoxy-D-glucitol (IX). Epoxide II was reduced with lithium aluminium hydride and the obtained 4-(adenin-9-yl)-1,6-anhydro-2,4-dideoxy-β-D-arabinohexopyranose (VII) on treatment with dilute hydrochloric acid and subsequent reduction with sodium borohydride gave 4-(adenin-9-yl)-2,4-dideoxy-D-arabino-hexitol (XI).